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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:57 UTC

HMDB ID

HMDB0015358

Secondary Accession Numbers

HMDB15358

Metabolite Identification

Common Name

Levomethadyl Acetate

Description

Levomethadyl Acetate is only found in individuals that have used or taken this drug. It is a narcotic analgesic with a long onset and duration of action. It is used mainly in the treatment of narcotic dependence. [PubChem]Opiate receptors (Mu, Kappa, Delta) are coupled with G-protein receptors and function as both positive and negative regulators of synaptic transmission via G-proteins that activate effector proteins. Binding of the opiate stimulates the exchange of GTP for GDP on the G-protein complex. As the effector system is adenylate cyclase and cAMP located at the inner surface of the plasma membrane, opioids decrease intracellular cAMP by inhibiting adenylate cyclase. Subsequently, the release of nociceptive neurotransmitters such as substance P, GABA, dopamine, acetylcholine and noradrenaline is inhibited. Opioids also inhibit the release of vasopressin, somatostatin, insulin and glucagon. Levomethadyl acetate effectively opens calcium-dependent inwardly rectifying potassium channels (OP1 receptor agonist), resulting in hyperpolarization and reduced neuronal excitability.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

1227
  Mrv0541 02231215202D          

 26 27  0  0  1  0            999 V2000
    5.8950   -0.7144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1325    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4253   -0.2482    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6575    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8325    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4825    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0572    0.2822    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6575    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6575   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8950    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9140    1.0946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9430    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3720   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3720    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9430   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7200    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.0341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5685   -1.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9430    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3720   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3720    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9430   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7200   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6575    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6575   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1325   -1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  6  0  0  0
  1 23  1  0  0  0  0
  2 23  2  0  0  0  0
  7  3  1  1  0  0  0
  3 17  1  0  0  0  0
  3 18  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
  5  7  1  0  0  0  0
  6 10  1  0  0  0  0
  7 11  1  0  0  0  0
  8 12  2  0  0  0  0
  8 14  1  0  0  0  0
  9 13  2  0  0  0  0
  9 15  1  0  0  0  0
 10 16  1  0  0  0  0
 12 19  1  0  0  0  0
 13 20  1  0  0  0  0
 14 21  2  0  0  0  0
 15 22  2  0  0  0  0
 19 24  2  0  0  0  0
 20 25  2  0  0  0  0
 21 24  1  0  0  0  0
 22 25  1  0  0  0  0
 23 26  1  0  0  0  0
M  END

HMDB0015358
     RDKit          3D
Levomethadyl Acetate
 57 58  0  0  0  0  0  0  0  0999 V2000
   -2.1479    2.0441   -2.4072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0142    1.1919   -1.9483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1855    0.7940   -0.4550 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2428    1.8920    0.3480 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2939    2.5209    0.9463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1654    3.7359    1.8076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4334    1.9979    0.7236 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2566   -0.3186   -0.2177 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1972   -0.0992   -0.4116 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9535    0.8573    0.4033 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6086    2.2978    0.3794 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3726    0.6248    0.0783 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8121   -0.6896    0.4374 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2367    1.6892    0.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7333   -1.3927   -1.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0527   -1.8664   -2.2122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4704   -2.8360   -3.0478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7757   -3.3027   -2.8598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5677   -2.8170   -1.8504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0192   -1.8361   -1.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4174   -1.0707    1.0746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9986   -0.6313    2.2032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0800   -1.4468    3.3375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5619   -2.7350    3.3298 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0279   -3.1873    2.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0957   -2.3707    1.0940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0492    3.1244   -2.1537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3160    2.0100   -3.5025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0849    1.6033   -1.9637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1651    0.2008   -2.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0116    1.5131   -2.1960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2414    0.3822   -0.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5424    3.5239    2.8183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7605    4.5725    1.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1275    4.0834    1.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4005    0.1983   -1.4909 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6830   -1.1103   -0.2618 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9369    0.5752    1.5184 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0845    2.6130    1.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1349    2.6546   -0.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5610    2.9417    0.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1118   -1.0890    1.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6971   -1.3686   -0.4294 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8600   -0.7326    0.7856 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2868    1.2492    0.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1286    2.1177    1.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2828    2.4234   -0.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0502   -1.5019   -2.3331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1124   -3.2428   -3.8491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2021   -4.0629   -3.5064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5878   -3.1722   -1.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6609   -1.4844   -0.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4140    0.3468    2.2920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5476   -1.0881    4.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6184   -3.3896    4.2141 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4379   -4.1836    2.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5682   -2.7531    0.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  3  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
  8 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  8 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 20 15  1  0
 26 21  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  6
  6 33  1  0
  6 34  1  0
  6 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  1
 11 39  1  0
 11 40  1  0
 11 41  1  0
 13 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 14 47  1  0
 16 48  1  0
 17 49  1  0
 18 50  1  0
 19 51  1  0
 20 52  1  0
 22 53  1  0
 23 54  1  0
 24 55  1  0
 25 56  1  0
 26 57  1  0
M  END

1227
  Mrv0541 02231215202D          

 26 27  0  0  1  0            999 V2000
    5.8950   -0.7144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1325    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4253   -0.2482    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6575    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8325    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4825    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0572    0.2822    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6575    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6575   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8950    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9140    1.0946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9430    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3720   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3720    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9430   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7200    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.0341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5685   -1.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9430    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3720   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3720    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9430   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7200   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6575    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6575   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1325   -1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  6  0  0  0
  1 23  1  0  0  0  0
  2 23  2  0  0  0  0
  7  3  1  1  0  0  0
  3 17  1  0  0  0  0
  3 18  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
  5  7  1  0  0  0  0
  6 10  1  0  0  0  0
  7 11  1  0  0  0  0
  8 12  2  0  0  0  0
  8 14  1  0  0  0  0
  9 13  2  0  0  0  0
  9 15  1  0  0  0  0
 10 16  1  0  0  0  0
 12 19  1  0  0  0  0
 13 20  1  0  0  0  0
 14 21  2  0  0  0  0
 15 22  2  0  0  0  0
 19 24  2  0  0  0  0
 20 25  2  0  0  0  0
 21 24  1  0  0  0  0
 22 25  1  0  0  0  0
 23 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015358

> <DATABASE_NAME>
hmdb

> <SMILES>
CC[C@H](OC(C)=O)C(C[C@H](C)N(C)C)(C1=CC=CC=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C23H31NO2/c1-6-22(26-19(3)25)23(17-18(2)24(4)5,20-13-9-7-10-14-20)21-15-11-8-12-16-21/h7-16,18,22H,6,17H2,1-5H3/t18-,22-/m0/s1

> <INCHI_KEY>
XBMIVRRWGCYBTQ-AVRDEDQJSA-N

> <FORMULA>
C23H31NO2

> <MOLECULAR_WEIGHT>
353.4977

> <EXACT_MASS>
353.235479241

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
40.5322514105547

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,6S)-6-(dimethylamino)-4,4-diphenylheptan-3-yl acetate

> <ALOGPS_LOGP>
4.78

> <JCHEM_LOGP>
4.884769339999999

> <ALOGPS_LOGS>
-5.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.869489670661055

> <JCHEM_POLAR_SURFACE_AREA>
29.54

> <JCHEM_REFRACTIVITY>
117.85760000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.79e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
levomethadyl acetate

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015358
     RDKit          3D
Levomethadyl Acetate
 57 58  0  0  0  0  0  0  0  0999 V2000
   -2.1479    2.0441   -2.4072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0142    1.1919   -1.9483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1855    0.7940   -0.4550 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2428    1.8920    0.3480 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2939    2.5209    0.9463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1654    3.7359    1.8076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4334    1.9979    0.7236 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2566   -0.3186   -0.2177 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1972   -0.0992   -0.4116 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9535    0.8573    0.4033 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6086    2.2978    0.3794 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3726    0.6248    0.0783 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8121   -0.6896    0.4374 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2367    1.6892    0.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7333   -1.3927   -1.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0527   -1.8664   -2.2122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4704   -2.8360   -3.0478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7757   -3.3027   -2.8598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5677   -2.8170   -1.8504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0192   -1.8361   -1.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4174   -1.0707    1.0746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9986   -0.6313    2.2032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0800   -1.4468    3.3375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5619   -2.7350    3.3298 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0279   -3.1873    2.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0957   -2.3707    1.0940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0492    3.1244   -2.1537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3160    2.0100   -3.5025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0849    1.6033   -1.9637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1651    0.2008   -2.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0116    1.5131   -2.1960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2414    0.3822   -0.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5424    3.5239    2.8183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7605    4.5725    1.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1275    4.0834    1.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4005    0.1983   -1.4909 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6830   -1.1103   -0.2618 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9369    0.5752    1.5184 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0845    2.6130    1.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1349    2.6546   -0.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5610    2.9417    0.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1118   -1.0890    1.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6971   -1.3686   -0.4294 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8600   -0.7326    0.7856 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2868    1.2492    0.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1286    2.1177    1.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2828    2.4234   -0.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0502   -1.5019   -2.3331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1124   -3.2428   -3.8491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2021   -4.0629   -3.5064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5878   -3.1722   -1.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6609   -1.4844   -0.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4140    0.3468    2.2920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5476   -1.0881    4.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6184   -3.3896    4.2141 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4379   -4.1836    2.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5682   -2.7531    0.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  3  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
  8 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  8 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 20 15  1  0
 26 21  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  6
  6 33  1  0
  6 34  1  0
  6 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  1
 11 39  1  0
 11 40  1  0
 11 41  1  0
 13 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 14 47  1  0
 16 48  1  0
 17 49  1  0
 18 50  1  0
 19 51  1  0
 20 52  1  0
 22 53  1  0
 23 54  1  0
 24 55  1  0
 25 56  1  0
 26 57  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1227                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      11.004  -1.334   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      13.314   0.000   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       4.527  -0.463   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       8.694   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.154   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.234   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.707   0.527   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.694   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.694  -1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.004   1.334   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.439   2.043   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.360   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.028  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.028   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.360  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.544   1.334   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.080   0.064   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.795  -1.980   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.360   3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.028  -3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.028   3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.360  -3.850   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.544  -1.334   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.694   4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.694  -4.620   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.314  -2.667   0.000  0.00  0.00           C+0
CONECT    1    6   23                                                       
CONECT    2   23                                                            
CONECT    3    7   17   18                                                  
CONECT    4    5    6    8    9                                             
CONECT    5    4    7                                                       
CONECT    6    1    4   10                                                  
CONECT    7    3    5   11                                                  
CONECT    8    4   12   14                                                  
CONECT    9    4   13   15                                                  
CONECT   10    6   16                                                       
CONECT   11    7                                                            
CONECT   12    8   19                                                       
CONECT   13    9   20                                                       
CONECT   14    8   21                                                       
CONECT   15    9   22                                                       
CONECT   16   10                                                            
CONECT   17    3                                                            
CONECT   18    3                                                            
CONECT   19   12   24                                                       
CONECT   20   13   25                                                       
CONECT   21   14   24                                                       
CONECT   22   15   25                                                       
CONECT   23    1    2   26                                                  
CONECT   24   19   21                                                       
CONECT   25   20   22                                                       
CONECT   26   23                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

COMPND    HMDB0015358
HETATM    1  C1  UNL     1      -2.148   2.044  -2.407  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.014   1.192  -1.948  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.186   0.794  -0.455  1.00  0.00           C  
HETATM    4  O1  UNL     1      -1.243   1.892   0.348  1.00  0.00           O  
HETATM    5  C4  UNL     1      -2.294   2.521   0.946  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.165   3.736   1.808  1.00  0.00           C  
HETATM    7  O2  UNL     1      -3.433   1.998   0.724  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.257  -0.319  -0.218  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.197  -0.099  -0.412  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.954   0.857   0.403  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.609   2.298   0.379  1.00  0.00           C  
HETATM   12  N1  UNL     1       3.373   0.625   0.078  1.00  0.00           N  
HETATM   13  C10 UNL     1       3.812  -0.690   0.437  1.00  0.00           C  
HETATM   14  C11 UNL     1       4.237   1.689   0.430  1.00  0.00           C  
HETATM   15  C12 UNL     1      -0.733  -1.393  -1.221  1.00  0.00           C  
HETATM   16  C13 UNL     1       0.053  -1.866  -2.212  1.00  0.00           C  
HETATM   17  C14 UNL     1      -0.470  -2.836  -3.048  1.00  0.00           C  
HETATM   18  C15 UNL     1      -1.776  -3.303  -2.860  1.00  0.00           C  
HETATM   19  C16 UNL     1      -2.568  -2.817  -1.850  1.00  0.00           C  
HETATM   20  C17 UNL     1      -2.019  -1.836  -1.015  1.00  0.00           C  
HETATM   21  C18 UNL     1      -0.417  -1.071   1.075  1.00  0.00           C  
HETATM   22  C19 UNL     1      -0.999  -0.631   2.203  1.00  0.00           C  
HETATM   23  C20 UNL     1      -1.080  -1.447   3.338  1.00  0.00           C  
HETATM   24  C21 UNL     1      -0.562  -2.735   3.330  1.00  0.00           C  
HETATM   25  C22 UNL     1       0.028  -3.187   2.192  1.00  0.00           C  
HETATM   26  C23 UNL     1       0.096  -2.371   1.094  1.00  0.00           C  
HETATM   27  H1  UNL     1      -2.049   3.124  -2.154  1.00  0.00           H  
HETATM   28  H2  UNL     1      -2.316   2.010  -3.502  1.00  0.00           H  
HETATM   29  H3  UNL     1      -3.085   1.603  -1.964  1.00  0.00           H  
HETATM   30  H4  UNL     1      -1.165   0.201  -2.477  1.00  0.00           H  
HETATM   31  H5  UNL     1      -0.012   1.513  -2.196  1.00  0.00           H  
HETATM   32  H6  UNL     1      -2.241   0.382  -0.496  1.00  0.00           H  
HETATM   33  H7  UNL     1      -2.542   3.524   2.818  1.00  0.00           H  
HETATM   34  H8  UNL     1      -2.761   4.572   1.392  1.00  0.00           H  
HETATM   35  H9  UNL     1      -1.127   4.083   1.860  1.00  0.00           H  
HETATM   36  H10 UNL     1       1.400   0.198  -1.491  1.00  0.00           H  
HETATM   37  H11 UNL     1       1.683  -1.110  -0.262  1.00  0.00           H  
HETATM   38  H12 UNL     1       1.937   0.575   1.518  1.00  0.00           H  
HETATM   39  H13 UNL     1       1.084   2.613   1.332  1.00  0.00           H  
HETATM   40  H14 UNL     1       1.135   2.655  -0.533  1.00  0.00           H  
HETATM   41  H15 UNL     1       2.561   2.942   0.464  1.00  0.00           H  
HETATM   42  H16 UNL     1       3.112  -1.089   1.228  1.00  0.00           H  
HETATM   43  H17 UNL     1       3.697  -1.369  -0.429  1.00  0.00           H  
HETATM   44  H18 UNL     1       4.860  -0.733   0.786  1.00  0.00           H  
HETATM   45  H19 UNL     1       5.287   1.249   0.434  1.00  0.00           H  
HETATM   46  H20 UNL     1       4.129   2.118   1.431  1.00  0.00           H  
HETATM   47  H21 UNL     1       4.283   2.423  -0.403  1.00  0.00           H  
HETATM   48  H22 UNL     1       1.050  -1.502  -2.333  1.00  0.00           H  
HETATM   49  H23 UNL     1       0.112  -3.243  -3.849  1.00  0.00           H  
HETATM   50  H24 UNL     1      -2.202  -4.063  -3.506  1.00  0.00           H  
HETATM   51  H25 UNL     1      -3.588  -3.172  -1.692  1.00  0.00           H  
HETATM   52  H26 UNL     1      -2.661  -1.484  -0.221  1.00  0.00           H  
HETATM   53  H27 UNL     1      -1.414   0.347   2.292  1.00  0.00           H  
HETATM   54  H28 UNL     1      -1.548  -1.088   4.238  1.00  0.00           H  
HETATM   55  H29 UNL     1      -0.618  -3.390   4.214  1.00  0.00           H  
HETATM   56  H30 UNL     1       0.438  -4.184   2.158  1.00  0.00           H  
HETATM   57  H31 UNL     1       0.568  -2.753   0.205  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3   30   31
CONECT    3    4    8   32
CONECT    4    5
CONECT    5    6    7    7
CONECT    6   33   34   35
CONECT    8    9   15   21
CONECT    9   10   36   37
CONECT   10   11   12   38
CONECT   11   39   40   41
CONECT   12   13   14
CONECT   13   42   43   44
CONECT   14   45   46   47
CONECT   15   16   16   20
CONECT   16   17   48
CONECT   17   18   18   49
CONECT   18   19   50
CONECT   19   20   20   51
CONECT   20   52
CONECT   21   22   22   26
CONECT   22   23   53
CONECT   23   24   24   54
CONECT   24   25   55
CONECT   25   26   26   56
CONECT   26   57
END

HMDB0015358
     RDKit          3D
Levomethadyl Acetate
 57 58  0  0  0  0  0  0  0  0999 V2000
   -2.1479    2.0441   -2.4072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0142    1.1919   -1.9483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1855    0.7940   -0.4550 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2428    1.8920    0.3480 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2939    2.5209    0.9463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1654    3.7359    1.8076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4334    1.9979    0.7236 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2566   -0.3186   -0.2177 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1972   -0.0992   -0.4116 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9535    0.8573    0.4033 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6086    2.2978    0.3794 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3726    0.6248    0.0783 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8121   -0.6896    0.4374 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2367    1.6892    0.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7333   -1.3927   -1.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0527   -1.8664   -2.2122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4704   -2.8360   -3.0478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7757   -3.3027   -2.8598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5677   -2.8170   -1.8504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0192   -1.8361   -1.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4174   -1.0707    1.0746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9986   -0.6313    2.2032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0800   -1.4468    3.3375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5619   -2.7350    3.3298 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0279   -3.1873    2.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0957   -2.3707    1.0940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0492    3.1244   -2.1537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3160    2.0100   -3.5025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0849    1.6033   -1.9637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1651    0.2008   -2.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0116    1.5131   -2.1960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2414    0.3822   -0.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5424    3.5239    2.8183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7605    4.5725    1.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1275    4.0834    1.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4005    0.1983   -1.4909 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6830   -1.1103   -0.2618 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9369    0.5752    1.5184 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0845    2.6130    1.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1349    2.6546   -0.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5610    2.9417    0.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1118   -1.0890    1.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6971   -1.3686   -0.4294 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8600   -0.7326    0.7856 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2868    1.2492    0.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1286    2.1177    1.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2828    2.4234   -0.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0502   -1.5019   -2.3331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1124   -3.2428   -3.8491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2021   -4.0629   -3.5064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5878   -3.1722   -1.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6609   -1.4844   -0.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4140    0.3468    2.2920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5476   -1.0881    4.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6184   -3.3896    4.2141 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4379   -4.1836    2.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5682   -2.7531    0.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  3  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
  8 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  8 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 20 15  1  0
 26 21  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  6
  6 33  1  0
  6 34  1  0
  6 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  1
 11 39  1  0
 11 40  1  0
 11 41  1  0
 13 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 14 47  1  0
 16 48  1  0
 17 49  1  0
 18 50  1  0
 19 51  1  0
 20 52  1  0
 22 53  1  0
 23 54  1  0
 24 55  1  0
 25 56  1  0
 26 57  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-alpha-Acetylmethadol	ChEBI
(1S,4S)-4-(Dimethylamino)-1-ethyl-2,2-diphenylpentyl acetate	ChEBI
1-alpha-Acetylmethadol	ChEBI
LAAM	ChEBI
Levacetilmetadol	ChEBI
Levacetylmethadolum	ChEBI
Levomethadyl	ChEBI
Orlaam	ChEBI
Levacetylmethadol	Kegg
(-)-a-Acetylmethadol	Generator
(-)-Α-acetylmethadol	Generator
(1S,4S)-4-(Dimethylamino)-1-ethyl-2,2-diphenylpentyl acetic acid	Generator
1-a-Acetylmethadol	Generator
1-Α-acetylmethadol	Generator
Levomethadyl acetic acid	Generator
Levo-alphacetylmethadol	HMDB
Levo-methadyl acetate	HMDB
Nor-laam	HMDB
Levo-alpha-acetylmethadol	HMDB
Levomethadyl acetate hydrochloride	HMDB
(3R,6R)-3-Acetoxy-6-dimethylamino-4,4-diphenylheptane	HMDB
Dimepheptanol	HMDB
6-(Dimethylamino)-4,4-diphenyl-3-heptanol acetate	HMDB
Alphacetylmethadol	HMDB
Levoacetylmethadol	HMDB
Methadol	HMDB
Acetylmethadol	HMDB
Amidolacetate	HMDB
Acemethadone	HMDB
Levo alpha acetylmethadol	HMDB
Methadyl acetate	HMDB

Chemical Formula

C₂₃H₃₁NO₂

Average Molecular Weight

353.4977

Monoisotopic Molecular Weight

353.235479241

IUPAC Name

(3S,6S)-6-(dimethylamino)-4,4-diphenylheptan-3-yl acetate

Traditional Name

levomethadyl acetate

CAS Registry Number

1477-40-3

SMILES

CC[C@H](OC(C)=O)C(C[C@H](C)N(C)C)(C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C23H31NO2/c1-6-22(26-19(3)25)23(17-18(2)24(4)5,20-13-9-7-10-14-20)21-15-11-8-12-16-21/h7-16,18,22H,6,17H2,1-5H3/t18-,22-/m0/s1

InChI Key

XBMIVRRWGCYBTQ-AVRDEDQJSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Substituents

Diphenylmethane
Aralkylamine
Amino acid or derivatives
Carboxylic acid ester
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Amine
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

tertiary amino compound (CHEBI:6441 )
acetate ester (CHEBI:6441 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015358)

Source

Exogenous

Exogenous (HMDB: HMDB0015358)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Levomethadyl Acetate Metabolism Pathway (PathBank: SMP0000638)

Drug action pathway

Levomethadyl Acetate Action Action Pathway (PathBank: SMP0000677)

Role

Industrial application

Opioid analgesic (HMDB: HMDB0015358)
Mu-opioid receptor antagonist (HMDB: HMDB0015358)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0018 g/L	Not Available
LogP	5.4	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0018 g/L	ALOGPS
logP	4.78	ALOGPS
logP	4.88	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Basic)	9.87	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	29.54 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	117.86 m³·mol⁻¹	ChemAxon
Polarizability	40.53 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	182.036	31661259
DarkChem	[M-H]-	181.598	31661259
DeepCCS	[M+H]+	189.234	30932474
DeepCCS	[M-H]-	186.876	30932474
DeepCCS	[M-2H]-	220.806	30932474
DeepCCS	[M+Na]+	195.916	30932474
AllCCS	[M+H]+	188.0	32859911
AllCCS	[M+H-H2O]+	185.1	32859911
AllCCS	[M+NH4]+	190.7	32859911
AllCCS	[M+Na]+	191.4	32859911
AllCCS	[M-H]-	195.2	32859911
AllCCS	[M+Na-2H]-	195.7	32859911
AllCCS	[M+HCOO]-	196.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Levomethadyl Acetate	CC[C@H](OC(C)=O)C(C[C@H](C)N(C)C)(C1=CC=CC=C1)C1=CC=CC=C1	3114.2	Standard polar	33892256
Levomethadyl Acetate	CC[C@H](OC(C)=O)C(C[C@H](C)N(C)C)(C1=CC=CC=C1)C1=CC=CC=C1	2275.6	Standard non polar	33892256
Levomethadyl Acetate	CC[C@H](OC(C)=O)C(C[C@H](C)N(C)C)(C1=CC=CC=C1)C1=CC=CC=C1	2236.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Levomethadyl Acetate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uk9-9081000000-c21fec0e8e70744482b4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Levomethadyl Acetate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Levomethadyl Acetate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levomethadyl Acetate 10V, Positive-QTOF	splash10-0udi-0029000000-c28a76d17f554d7ba439	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levomethadyl Acetate 20V, Positive-QTOF	splash10-022c-7096000000-e5337d3be9cfb3f23f09	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levomethadyl Acetate 40V, Positive-QTOF	splash10-0fkc-5190000000-113274c2b46b6767d5b3	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levomethadyl Acetate 10V, Negative-QTOF	splash10-0udi-1019000000-248c95ec24dae3299384	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levomethadyl Acetate 20V, Negative-QTOF	splash10-0nmi-4039000000-abf719229500214241e6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levomethadyl Acetate 40V, Negative-QTOF	splash10-05mo-9081000000-e357c686965cbd06e26c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levomethadyl Acetate 10V, Positive-QTOF	splash10-0udi-0089000000-c427737dde1e774f4972	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levomethadyl Acetate 20V, Positive-QTOF	splash10-0pb9-2193000000-2a568014680a63d6012f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levomethadyl Acetate 40V, Positive-QTOF	splash10-06di-3790000000-c1eca86692e210363e6a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levomethadyl Acetate 10V, Negative-QTOF	splash10-0zfr-6019000000-270678fc70b14132747a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levomethadyl Acetate 20V, Negative-QTOF	splash10-0a4i-9000000000-c01bbbf5bed889264ddb	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levomethadyl Acetate 40V, Negative-QTOF	splash10-056r-2930000000-da1f57c344e66e9ff112	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Levomethadyl Acetate Metabolism Pathway		Not Available
Levomethadyl Acetate Action Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01227	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01227	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01227

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

14401

KEGG Compound ID

C08012

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Levomethadyl_Acetate

METLIN ID

Not Available

PubChem Compound

15130

PDB ID

Not Available

ChEBI ID

6441

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Skoulis NP, James RC, Harbison RD, Roberts SM: Depression of hepatic glutathione by opioid analgesic drugs in mice. Toxicol Appl Pharmacol. 1989 Jun 1;99(1):139-47. [PubMed:2471291 ]
Johnson RE, Chutuape MA, Strain EC, Walsh SL, Stitzer ML, Bigelow GE: A comparison of levomethadyl acetate, buprenorphine, and methadone for opioid dependence. N Engl J Med. 2000 Nov 2;343(18):1290-7. [PubMed:11058673 ]
Kreek MJ, Vocci FJ: History and current status of opioid maintenance treatments: blending conference session. J Subst Abuse Treat. 2002 Sep;23(2):93-105. [PubMed:12220607 ]
Kuo I, Brady J, Butler C, Schwartz R, Brooner R, Vlahov D, Strathdee SA: Feasibility of referring drug users from a needle exchange program into an addiction treatment program: experience with a mobile treatment van and LAAM maintenance. J Subst Abuse Treat. 2003 Jan;24(1):67-74. [PubMed:12646332 ]
Deshmukh SV, Nanovskaya TN, Hankins GD, Ahmed MS: N-demethylation of levo-alpha-acetylmethadol by human placental aromatase. Biochem Pharmacol. 2004 Mar 1;67(5):885-92. [PubMed:15104241 ]
Nanovskaya TN, Deshmukh SV, Miles R, Burmaster S, Ahmed MS: Transfer of L-alpha-acetylmethadol (LAAM) and L-alpha-acetyl-N-normethadol (norLAAM) by the perfused human placental lobule. J Pharmacol Exp Ther. 2003 Jul;306(1):205-12. Epub 2003 Apr 3. [PubMed:12676878 ]
Law F: Review: levomethadyl acetate hydrochloride improves retention in treatment and reduces heroin use in heroin dependence. Evid Based Ment Health. 2002 Nov;5(4):107. [PubMed:12440445 ]
McCance-Katz EF, Rainey PM, Smith P, Morse G, Friedland G, Gourevitch M, Jatlow P: Drug interactions between opioids and antiretroviral medications: interaction between methadone, LAAM, and nelfinavir. Am J Addict. 2004 Mar-Apr;13(2):163-80. [PubMed:15204667 ]
Cone EJ, Preston KL: Toxicologic aspects of heroin substitution treatment. Ther Drug Monit. 2002 Apr;24(2):193-8. [PubMed:11897965 ]
Neff JA, Moody DE: Differential N-demethylation of l-alpha-acetylmethadol (LAAM) and norLAAM by cytochrome P450s 2B6, 2C18, and 3A4. Biochem Biophys Res Commun. 2001 Jun 15;284(3):751-6. [PubMed:11396966 ]
Thomas BF, Jeffcoat AR, Myers MW, Mathews JM, Cook CE: Determination of l-alpha-acetylmethadol, l-alpha-noracetylmethadol and l-alpha-dinoracetylmethadol in plasma by gas chromatography-mass spectrometry. J Chromatogr B Biomed Appl. 1994 May 13;655(2):201-11. [PubMed:8081466 ]
Grevert P, Masover B, Goldstein A: Failure of methadone and levomethadyl acetate (levo-alpha-acetylmethadol, LAAM) maintenance to affect memory. Arch Gen Psychiatry. 1977 Jul;34(7):849-53. [PubMed:879977 ]
Vocci F, Ling W: Medications development: successes and challenges. Pharmacol Ther. 2005 Oct;108(1):94-108. [PubMed:16083966 ]
Moody DE, Crouch DJ, Sakashita CO, Alburges ME, Minear K, Schulthies JE, Foltz RL: A gas chromatographic-positive ion chemical ionization-mass spectrometric method for the determination of I-alpha-acetylmethadol (LAAM), norLAAM, and dinorLAAM in plasma, urine, and tissue. J Anal Toxicol. 1995 Oct;19(6):343-51. [PubMed:8926727 ]
Judson BA, Himmelberger DU, Goldstein A: The naloxone test for opiate dependence. Clin Pharmacol Ther. 1980 Apr;27(4):492-501. [PubMed:7357808 ]
Eap CB, Bouchoux G, Scherbaum N, Gastpar M, Powell Golay K, Baumann P: Determination of human plasma levels of levo-alpha-acetylmethadol and its metabolites by gas chromatography-mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 Jun 5;805(1):141-6. [PubMed:15113550 ]
Nelson AC, Huang W, Moody DE: Variables in human liver microsome preparation: impact on the kinetics of l-alpha-acetylmethadol (LAAM) n-demethylation and dextromethorphan O-demethylation. Drug Metab Dispos. 2001 Mar;29(3):319-25. [PubMed:11181502 ]
Eissenberg T, Bigelow GE, Strain EC, Walsh SL, Brooner RK, Stitzer ML, Johnson RE: Dose-related efficacy of levomethadyl acetate for treatment of opioid dependence. A randomized clinical trial. JAMA. 1997 Jun 25;277(24):1945-51. [PubMed:9200635 ]
Cheever ML, Armendariz GA, Moody DE: Detection of methadone, LAAM, and their metabolites by methadone immunoassays. J Anal Toxicol. 1999 Oct;23(6):500-5. [PubMed:10517557 ]
York RG, Denny KH, Moody DE, Alburges ME: Developmental toxicity of levo-alpha-acetylmethadol (LAAM) in tolerant rats. Int J Toxicol. 2002 Mar-Apr;21(2):147-59. [PubMed:12022632 ]
Moody DE, Alburges ME, Parker RJ, Collins JM, Strong JM: The involvement of cytochrome P450 3A4 in the N-demethylation of L-alpha-acetylmethadol (LAAM), norLAAM, and methadone. Drug Metab Dispos. 1997 Dec;25(12):1347-53. [PubMed:9394023 ]
Krantz MJ, Mehler PS: Treating opioid dependence. Growing implications for primary care. Arch Intern Med. 2004 Feb 9;164(3):277-88. [PubMed:14769623 ]
Deamer RL, Wilson DR, Clark DS, Prichard JG: Torsades de pointes associated with high dose levomethadyl acetate (ORLAAM). J Addict Dis. 2001;20(4):7-14. [PubMed:11760927 ]
Borzelleca JF, Egle JL Jr, Harris LS, Belleville JA: Toxicological evaluation of mu-agonists. Part II: Assessment of toxicity following 30 days of repeated oral dosing of male and female rats with levo-alpha-noracetylmethadol HCl (NorLAAM). J Appl Toxicol. 1995 Sep-Oct;15(5):339-55. [PubMed:8666717 ]
Huang W, Bemis PA, Slawson MH, Moody DE: Determination of l-alpha-acetylmethadol (LAAM), norLAAM, and dinorLAAM in clinical and in vitro samples using liquid chromatography with electrospray ionization and tandem mass spectrometry. J Pharm Sci. 2003 Jan;92(1):10-20. [PubMed:12486677 ]
Wilkins DG, Valdez AS, Krueger GG, Rollins DE: Quantitative analysis of l-alpha-acetylmethadol, l-alpha-acetyl-N-normethadol, and l-alpha-acetyl-N,N-dinormethadol in human hair by positive ion chemical ionization mass spectrometry. J Anal Toxicol. 1997 Oct;21(6):420-6. [PubMed:9323520 ]
Jaffe JH, O'Keeffe C: From morphine clinics to buprenorphine: regulating opioid agonist treatment of addiction in the United States. Drug Alcohol Depend. 2003 May 21;70(2 Suppl):S3-11. [PubMed:12738346 ]
Authors unspecified: Levomethadyl acetate to be used in narcotic treatment programs. Clin Pharm. 1993 Nov;12(11):797, 800. [PubMed:8275644 ]
Jones HE, Strain EC, Bigelow GE, Walsh SL, Stitzer ML, Eissenberg T, Johnson RE: Induction with levomethadyl acetate: safety and efficacy. Arch Gen Psychiatry. 1998 Aug;55(8):729-36. [PubMed:9707384 ]
Lott DC, Strain EC, Brooner RK, Bigelow GE, Johnson RE: HIV risk behaviors during pharmacologic treatment for opioid dependence: a comparison of levomethadyl acetate [corrected] buprenorphine, and methadone. J Subst Abuse Treat. 2006 Sep;31(2):187-94. Epub 2006 Jul 18. [PubMed:16919747 ]
Vocci FJ, Acri J, Elkashef A: Medication development for addictive disorders: the state of the science. Am J Psychiatry. 2005 Aug;162(8):1432-40. [PubMed:16055764 ]
McCance-Katz EF, Rainey PM, Smith P, Morse GD, Friedland G, Boyarsky B, Gourevitch M, Jatlow P: Drug interactions between opioids and antiretroviral medications: interaction between methadone, LAAM, and delavirdine. Am J Addict. 2006 Jan-Feb;15(1):23-34. [PubMed:16449090 ]
Moody DE, Monti KM, Spanbauer AC: Long-term stability of abused drugs and antiabuse chemotherapeutical agents stored at -20 degrees C. J Anal Toxicol. 1999 Oct;23(6):535-40. [PubMed:10517563 ]
Borg L, Ho A, Wells A, Joseph H, Appel P, Moody D, Kreek MJ: The use of levo-alpha-acetylmethadol (LAAM) in methadone patients who have not achieved heroin abstinence. J Addict Dis. 2002;21(3):13-22. [PubMed:12094997 ]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Oda Y, Kharasch ED: Metabolism of methadone and levo-alpha-acetylmethadol (LAAM) by human intestinal cytochrome P450 3A4 (CYP3A4): potential contribution of intestinal metabolism to presystemic clearance and bioactivation. J Pharmacol Exp Ther. 2001 Sep;298(3):1021-32. [PubMed:11504799 ]

Enzyme Details

2. Cytochrome P450 3A5

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A5
Uniprot ID:: P20815
Molecular weight:: 57108.065

Enzyme Details

3. Cytochrome P450 3A7

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A7
Uniprot ID:: P24462
Molecular weight:: 57525.03

Enzyme Details

4. Cytochrome P450 19A1

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:: CYP19A1
Uniprot ID:: P11511
Molecular weight:: 57882.48

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

5. Mu-type opioid receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for beta-endorphin
Gene Name:: OPRM1
Uniprot ID:: P35372
Molecular weight:: 44778.9

References

Yu Y, Zhang L, Yin X, Sun H, Uhl GR, Wang JB: Mu opioid receptor phosphorylation, desensitization, and ligand efficacy. J Biol Chem. 1997 Nov 14;272(46):28869-74. [PubMed:9360954 ]
Skoulis NP, James RC, Harbison RD, Roberts SM: Depression of hepatic glutathione by opioid analgesic drugs in mice. Toxicol Appl Pharmacol. 1989 Jun 1;99(1):139-47. [PubMed:2471291 ]
Kreek MJ: Methadone-related opioid agonist pharmacotherapy for heroin addiction. History, recent molecular and neurochemical research and future in mainstream medicine. Ann N Y Acad Sci. 2000;909:186-216. [PubMed:10911931 ]
Xiao Y, Smith RD, Caruso FS, Kellar KJ: Blockade of rat alpha3beta4 nicotinic receptor function by methadone, its metabolites, and structural analogs. J Pharmacol Exp Ther. 2001 Oct;299(1):366-71. [PubMed:11561100 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Levomethadyl Acetate (HMDB0015358)

MOL for HMDB0015358 (Levomethadyl Acetate)

3D MOL for HMDB0015358 (Levomethadyl Acetate)

3D SDF for HMDB0015358 (Levomethadyl Acetate)

3D-SDF for HMDB0015358 (Levomethadyl Acetate)

PDB for HMDB0015358 (Levomethadyl Acetate)

3D PDB for HMDB0015358 (Levomethadyl Acetate)

SMILES for HMDB0015358 (Levomethadyl Acetate)

INCHI for HMDB0015358 (Levomethadyl Acetate)

Structure for HMDB0015358 (Levomethadyl Acetate)

3D Structure for HMDB0015358 (Levomethadyl Acetate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References