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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:37:14 UTC

Update Date

2021-09-26 23:08:18 UTC

HMDB ID

HMDB0254357

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N-Methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine

Description

MBDB belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms. MBDB is a closely related chemical analogue of MDMA, with the only difference between the two molecules being an ethyl group instead of a methyl group attached to the alpha carbon. MBDB is a very strong basic compound (based on its pKa). Its metabolism has been described in scientific literature. MBDB was first synthesized by pharmacologist and medicinal chemist David E. Nichols and later tested by Alexander Shulgin and described in his book, PiHKAL: A Chemical Love Story. Scheduling of MBDB was therefore not recommended.MBDB is considered a Schedule 9 Prohibited substance in Australia under the Poisons Standard (October 2015). The thirty-second meeting of the WHO Expert Committee on Drug Dependence (September 2000) evaluated MBDB and recommended against scheduling. MBDB tends to produce less euphoria, psychedelia, and stimulation in comparison to MDMA.Unlike MDMA, MBDB is not internationally scheduled under the United Nations Convention on Psychotropic Substances. 1,3-Benzodioxolyl-N-methylbutanamine (N-methyl-1,3-benzodioxolylbutanamine, MBDB, 3,4-methylenedioxy-N-methyl-α-ethylphenylethylamine) is an entactogen of the phenethylamine chemical class. This compound has been identified in human blood as reported by (PMID: 31557052 ). N-methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically N-Methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0254357
     RDKit          3D
N-Methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine
 32 33  0  0  0  0  0  0  0  0999 V2000
   -4.0752   -0.0282    0.5089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9081   -0.8299    0.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5477   -0.2510    0.3167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5727   -1.3272   -0.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8292   -0.9569   -0.0631 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4903   -1.2843    1.1080 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8295   -0.9476    1.2739 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5341   -0.2805    0.2805 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8873    0.0445   -0.8756 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5603   -0.2991   -1.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7559    0.7067   -1.7471 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9574    0.9399   -1.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8385    0.1774    0.1551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3663    0.9678   -0.3561 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1146    2.1088   -0.0434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3820    0.8047   -0.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9429    0.2332    1.6001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9931   -0.7169    0.5010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0640   -1.0401   -1.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0029   -1.8599    0.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3725   -0.2051    1.4115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8566   -1.6114   -1.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7767   -2.2213    0.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9972   -1.8014    1.9132 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3693   -1.1888    2.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0714   -0.0340   -1.9388 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8077    0.5602   -1.6628 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0322    2.0226   -0.8418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0420    0.8946   -1.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5025    3.0552    0.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8070    2.3350   -0.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6338    2.0328    0.9056 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
  3 14  1  0
 14 15  1  0
 10  5  1  0
 13  8  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
 10 26  1  0
 12 27  1  0
 12 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
M  END


  Mrv1652306031607142D          

 15 16  0  0  0  0            999 V2000
    6.8513   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  5  4  2  0  0  0  0
  9  4  1  0  0  0  0
  9  6  1  0  0  0  0
  9  7  2  0  0  0  0
 10  3  1  0  0  0  0
 10  6  1  0  0  0  0
 11  5  1  0  0  0  0
 12  7  1  0  0  0  0
 12 11  2  0  0  0  0
 13  2  1  0  0  0  0
 13 10  1  0  0  0  0
 14  8  1  0  0  0  0
 14 11  1  0  0  0  0
 15  8  1  0  0  0  0
 15 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254357

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(CC1=CC2=C(OCO2)C=C1)NC

> <INCHI_IDENTIFIER>
InChI=1S/C12H17NO2/c1-3-10(13-2)6-9-4-5-11-12(7-9)15-8-14-11/h4-5,7,10,13H,3,6,8H2,1-2H3

> <INCHI_KEY>
USWVWJSAJAEEHQ-UHFFFAOYSA-N

> <FORMULA>
C12H17NO2

> <MOLECULAR_WEIGHT>
207.273

> <EXACT_MASS>
207.125928791

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
23.301564234209053

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[1-(2H-1,3-benzodioxol-5-yl)butan-2-yl](methyl)amine

> <ALOGPS_LOGP>
2.24

> <JCHEM_LOGP>
2.382586738

> <ALOGPS_LOGS>
-2.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.275522001911291

> <JCHEM_POLAR_SURFACE_AREA>
30.49

> <JCHEM_REFRACTIVITY>
58.770700000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.17e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methylbenzodioxolylbutanamine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0254357
     RDKit          3D
N-Methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine
 32 33  0  0  0  0  0  0  0  0999 V2000
   -4.0752   -0.0282    0.5089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9081   -0.8299    0.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5477   -0.2510    0.3167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5727   -1.3272   -0.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8292   -0.9569   -0.0631 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4903   -1.2843    1.1080 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8295   -0.9476    1.2739 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5341   -0.2805    0.2805 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8873    0.0445   -0.8756 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5603   -0.2991   -1.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7559    0.7067   -1.7471 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9574    0.9399   -1.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8385    0.1774    0.1551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3663    0.9678   -0.3561 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1146    2.1088   -0.0434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3820    0.8047   -0.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9429    0.2332    1.6001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9931   -0.7169    0.5010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0640   -1.0401   -1.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0029   -1.8599    0.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3725   -0.2051    1.4115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8566   -1.6114   -1.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7767   -2.2213    0.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9972   -1.8014    1.9132 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3693   -1.1888    2.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0714   -0.0340   -1.9388 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8077    0.5602   -1.6628 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0322    2.0226   -0.8418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0420    0.8946   -1.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5025    3.0552    0.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8070    2.3350   -0.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6338    2.0328    0.9056 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
  3 14  1  0
 14 15  1  0
 10  5  1  0
 13  8  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
 10 26  1  0
 12 27  1  0
 12 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
M  END

HEADER    PROTEIN                                 03-JUN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-16         0                                  
HETATM    1  C   UNK     0      12.789  -0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.788   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.455  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.788  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.122  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      10.122   1.540   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0       3.322   2.016   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       3.322  -0.476   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   13                                                            
CONECT    3    1   10                                                       
CONECT    4    5    9                                                       
CONECT    5    4   11                                                       
CONECT    6    9   10                                                       
CONECT    7    9   12                                                       
CONECT    8   14   15                                                       
CONECT    9    4    6    7                                                  
CONECT   10    3    6   13                                                  
CONECT   11    5   12   14                                                  
CONECT   12    7   11   15                                                  
CONECT   13    2   10                                                       
CONECT   14    8   11                                                       
CONECT   15    8   12                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0254357
HETATM    1  C1  UNL     1      -4.075  -0.028   0.509  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.908  -0.830   0.076  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.548  -0.251   0.317  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.573  -1.327  -0.209  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.829  -0.957  -0.063  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.490  -1.284   1.108  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.830  -0.948   1.274  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.534  -0.281   0.281  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.887   0.045  -0.876  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.560  -0.299  -1.018  1.00  0.00           C  
HETATM   11  O1  UNL     1       3.756   0.707  -1.747  1.00  0.00           O  
HETATM   12  C11 UNL     1       4.957   0.940  -1.037  1.00  0.00           C  
HETATM   13  O2  UNL     1       4.839   0.177   0.155  1.00  0.00           O  
HETATM   14  N1  UNL     1      -1.366   0.968  -0.356  1.00  0.00           N  
HETATM   15  C12 UNL     1      -2.115   2.109  -0.043  1.00  0.00           C  
HETATM   16  H1  UNL     1      -4.382   0.805  -0.119  1.00  0.00           H  
HETATM   17  H2  UNL     1      -3.943   0.233   1.600  1.00  0.00           H  
HETATM   18  H3  UNL     1      -4.993  -0.717   0.501  1.00  0.00           H  
HETATM   19  H4  UNL     1      -3.064  -1.040  -1.033  1.00  0.00           H  
HETATM   20  H5  UNL     1      -3.003  -1.860   0.519  1.00  0.00           H  
HETATM   21  H6  UNL     1      -1.372  -0.205   1.411  1.00  0.00           H  
HETATM   22  H7  UNL     1      -0.857  -1.611  -1.249  1.00  0.00           H  
HETATM   23  H8  UNL     1      -0.777  -2.221   0.415  1.00  0.00           H  
HETATM   24  H9  UNL     1       0.997  -1.801   1.913  1.00  0.00           H  
HETATM   25  H10 UNL     1       3.369  -1.189   2.172  1.00  0.00           H  
HETATM   26  H11 UNL     1       1.071  -0.034  -1.939  1.00  0.00           H  
HETATM   27  H12 UNL     1       5.808   0.560  -1.663  1.00  0.00           H  
HETATM   28  H13 UNL     1       5.032   2.023  -0.842  1.00  0.00           H  
HETATM   29  H14 UNL     1      -1.042   0.895  -1.345  1.00  0.00           H  
HETATM   30  H15 UNL     1      -1.503   3.055   0.012  1.00  0.00           H  
HETATM   31  H16 UNL     1      -2.807   2.335  -0.909  1.00  0.00           H  
HETATM   32  H17 UNL     1      -2.634   2.033   0.906  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3   19   20
CONECT    3    4   14   21
CONECT    4    5   22   23
CONECT    5    6    6   10
CONECT    6    7   24
CONECT    7    8    8   25
CONECT    8    9   13
CONECT    9   10   10   11
CONECT   10   26
CONECT   11   12
CONECT   12   13   27   28
CONECT   14   15   29
CONECT   15   30   31   32
END

HMDB0254357
     RDKit          3D
N-Methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine
 32 33  0  0  0  0  0  0  0  0999 V2000
   -4.0752   -0.0282    0.5089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9081   -0.8299    0.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5477   -0.2510    0.3167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5727   -1.3272   -0.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8292   -0.9569   -0.0631 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4903   -1.2843    1.1080 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8295   -0.9476    1.2739 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5341   -0.2805    0.2805 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8873    0.0445   -0.8756 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5603   -0.2991   -1.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7559    0.7067   -1.7471 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9574    0.9399   -1.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8385    0.1774    0.1551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3663    0.9678   -0.3561 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1146    2.1088   -0.0434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3820    0.8047   -0.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9429    0.2332    1.6001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9931   -0.7169    0.5010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0640   -1.0401   -1.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0029   -1.8599    0.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3725   -0.2051    1.4115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8566   -1.6114   -1.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7767   -2.2213    0.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9972   -1.8014    1.9132 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3693   -1.1888    2.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0714   -0.0340   -1.9388 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8077    0.5602   -1.6628 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0322    2.0226   -0.8418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0420    0.8946   -1.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5025    3.0552    0.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8070    2.3350   -0.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6338    2.0328    0.9056 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
  3 14  1  0
 14 15  1  0
 10  5  1  0
 13  8  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
 10 26  1  0
 12 27  1  0
 12 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-Methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine, (S)-isomer	MeSH
N-Methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine	MeSH
N-Methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine, (R)-isomer	MeSH

Chemical Formula

C₁₂H₁₇NO₂

Average Molecular Weight

207.273

Monoisotopic Molecular Weight

207.125928791

IUPAC Name

[1-(2H-1,3-benzodioxol-5-yl)butan-2-yl](methyl)amine

Traditional Name

methylbenzodioxolylbutanamine

CAS Registry Number

Not Available

SMILES

CCC(CC1=CC2=C(OCO2)C=C1)NC

InChI Identifier

InChI=1S/C12H17NO2/c1-3-10(13-2)6-9-4-5-11-12(7-9)15-8-14-11/h4-5,7,10,13H,3,6,8H2,1-2H3

InChI Key

USWVWJSAJAEEHQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodioxoles

Sub Class

Not Available

Direct Parent

Benzodioxoles

Alternative Parents

Substituents

Benzodioxole
Aralkylamine
Benzenoid
Oxacycle
Secondary amine
Secondary aliphatic amine
Acetal
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.24	ALOGPS
logP	2.38	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Basic)	10.28	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	30.49 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	58.77 m³·mol⁻¹	ChemAxon
Polarizability	23.3 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
DeepCCS	[M+H]+	146.801	30932474
DeepCCS	[M-H]-	144.443	30932474
DeepCCS	[M-2H]-	178.68	30932474
DeepCCS	[M+Na]+	153.777	30932474
AllCCS	[M+H]+	147.7	32859911
AllCCS	[M+H-H2O]+	143.6	32859911
AllCCS	[M+NH4]+	151.6	32859911
AllCCS	[M+Na]+	152.7	32859911
AllCCS	[M-H]-	152.1	32859911
AllCCS	[M+Na-2H]-	152.5	32859911
AllCCS	[M+HCOO]-	153.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine	CCC(CC1=CC2=C(OCO2)C=C1)NC	2423.5	Standard polar	33892256
N-Methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine	CCC(CC1=CC2=C(OCO2)C=C1)NC	1663.8	Standard non polar	33892256
N-Methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine	CCC(CC1=CC2=C(OCO2)C=C1)NC	1595.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine,1TMS,isomer #1	CCC(CC1=CC=C2OCOC2=C1)N(C)[Si](C)(C)C	1788.7	Semi standard non polar	33892256
N-Methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine,1TMS,isomer #1	CCC(CC1=CC=C2OCOC2=C1)N(C)[Si](C)(C)C	1780.9	Standard non polar	33892256
N-Methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine,1TMS,isomer #1	CCC(CC1=CC=C2OCOC2=C1)N(C)[Si](C)(C)C	2406.5	Standard polar	33892256
N-Methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine,1TBDMS,isomer #1	CCC(CC1=CC=C2OCOC2=C1)N(C)[Si](C)(C)C(C)(C)C	2021.8	Semi standard non polar	33892256
N-Methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine,1TBDMS,isomer #1	CCC(CC1=CC=C2OCOC2=C1)N(C)[Si](C)(C)C(C)(C)C	2026.5	Standard non polar	33892256
N-Methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine,1TBDMS,isomer #1	CCC(CC1=CC=C2OCOC2=C1)N(C)[Si](C)(C)C(C)(C)C	2536.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00bc-9400000000-d48710efd14c364344fe	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine 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 - N-Methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine 10V, Positive-QTOF	splash10-0a4i-0390000000-5251b1bcf0f67b4b37a6	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine 20V, Positive-QTOF	splash10-0a4i-3980000000-90e1a6c2fc0e3c30bcbd	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine 40V, Positive-QTOF	splash10-0083-9700000000-766feefc8150f6ba95e5	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine 10V, Negative-QTOF	splash10-0a4i-0090000000-59a47619afbec85f44c7	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine 20V, Negative-QTOF	splash10-0a4i-0390000000-5465b240e77b87dea1e9	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine 40V, Negative-QTOF	splash10-00al-6900000000-bea705fcbd6ce047d362	2019-02-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

MBDB

METLIN ID

Not Available

PubChem Compound

124844

PDB ID

Not Available

ChEBI ID

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for N-Methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine (HMDB0254357)

MOL for HMDB0254357 (N-Methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine)

3D MOL for HMDB0254357 (N-Methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine)

3D SDF for HMDB0254357 (N-Methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine)

3D-SDF for HMDB0254357 (N-Methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine)

PDB for HMDB0254357 (N-Methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine)

3D PDB for HMDB0254357 (N-Methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine)

SMILES for HMDB0254357 (N-Methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine)

INCHI for HMDB0254357 (N-Methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine)

Structure for HMDB0254357 (N-Methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine)

3D Structure for HMDB0254357 (N-Methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra