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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-04-06 16:19:41 UTC

Update Date

2023-02-21 17:17:38 UTC

HMDB ID

HMDB0012128

Secondary Accession Numbers

HMDB12128

Metabolite Identification

Common Name

(R)-Amphetamine

Description

(R)-amphetamine is an enantiomer of amphetamine that is urinary metabolite from selegeline (drug used for the treatment of early-stage Parkinson's disease, depression and senile dementia). (R)-amphetamine as stereoisomer is not considered psychoactive and has little abuse potential. The stimulatory effect on locomotor activity and dopamine synthesis may be contributed to by the action of R-methamphetamine. If anyone is prescribed and takes selegiline, they can and will test positive for amphetamine/methamphetamine on most drug tests.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(-)-Amphetamine	ChEBI
(-)-Phenylisopropylamine	ChEBI
(R)-alpha-Methylbenzeneethanamine	ChEBI
(R)-alpha-Methylphenethylamine	ChEBI
Levamfetamine	ChEBI
Levamphetamine	ChEBI
(R)-a-Methylbenzeneethanamine	Generator
(R)-Α-methylbenzeneethanamine	Generator
(R)-a-Methylphenethylamine	Generator
(R)-Α-methylphenethylamine	Generator
Amfetamine	MeSH
Amphetamine	MeSH
Amphetamine sulfate	MeSH
Amphetamine sulfate (2:1)	MeSH
Centramina	MeSH
Desoxynorephedrin	MeSH
Fenamine	MeSH
Levoamphetamine	MeSH
Mydrial	MeSH
Phenamine	MeSH
Phenopromin	MeSH
Sulfate, amphetamine	MeSH
Thyramine	MeSH
L Amphetamine	MeSH
Levo amphetamine	MeSH
Levo-amphetamine	MeSH
(R)-a-Methyl-benzeneethanamine	HMDB
(R)-alpha-Methyl-benzeneethanamine	HMDB
(R)-Phenaminum	HMDB
(R)-Phenylisopropylamine	HMDB
L-(R)-Amphetamine	HMDB
L-a-Methylphenethylamine	HMDB
L-alpha-Methylphenethylamine	HMDB
L-Amphetamine	HMDB
Miquel brand OF amfetamine sulfate	MeSH, HMDB

Chemical Formula

C₉H₁₃N

Average Molecular Weight

135.2062

Monoisotopic Molecular Weight

135.104799421

IUPAC Name

(2R)-1-phenylpropan-2-amine

Traditional Name

(-)-amphetamine

CAS Registry Number

156-34-3

SMILES

C[C@@H](N)CC1=CC=CC=C1

InChI Identifier

InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3/t8-/m1/s1

InChI Key

KWTSXDURSIMDCE-MRVPVSSYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenethylamines

Direct Parent

Amphetamines and derivatives

Alternative Parents

Substituents

Amphetamine or derivatives
Phenylpropane
Aralkylamine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organonitrogen compound
Primary aliphatic amine
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

amphetamine (CHEBI:42724 )

Ontology

Not Available

Exogenous (HMDB: HMDB0012128)

Process

Not Available

Role

Industrial application

Drug (HMDB: HMDB0012128)

Physical Properties

State

Solid

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
Water Solubility	1.74 g/L	ALOGPS
logP	1.85	ALOGPS
logP	1.8	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Basic)	10.01	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	26.02 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	43.71 m³·mol⁻¹	ChemAxon
Polarizability	16.18 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	130.752	31661259
DarkChem	[M-H]-	127.692	31661259
DeepCCS	[M+H]+	133.022	30932474
DeepCCS	[M-H]-	130.159	30932474
DeepCCS	[M-2H]-	166.352	30932474
DeepCCS	[M+Na]+	141.755	30932474
AllCCS	[M+H]+	129.1	32859911
AllCCS	[M+H-H2O]+	124.5	32859911
AllCCS	[M+NH4]+	133.5	32859911
AllCCS	[M+Na]+	134.8	32859911
AllCCS	[M-H]-	131.1	32859911
AllCCS	[M+Na-2H]-	132.9	32859911
AllCCS	[M+HCOO]-	134.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.74 minutes	32390414
Predicted by Siyang on May 30, 2022	10.3939 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.71 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	72.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1049.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	346.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	124.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	200.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	93.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	309.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	346.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	177.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	869.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	313.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	816.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	218.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	276.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	361.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	326.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	39.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(R)-Amphetamine	C[C@@H](N)CC1=CC=CC=C1	1645.8	Standard polar	33892256
(R)-Amphetamine	C[C@@H](N)CC1=CC=CC=C1	1128.0	Standard non polar	33892256
(R)-Amphetamine	C[C@@H](N)CC1=CC=CC=C1	1147.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(R)-Amphetamine,1TMS,isomer #1	C[C@H](CC1=CC=CC=C1)N[Si](C)(C)C	1334.7	Semi standard non polar	33892256
(R)-Amphetamine,1TMS,isomer #1	C[C@H](CC1=CC=CC=C1)N[Si](C)(C)C	1339.0	Standard non polar	33892256
(R)-Amphetamine,1TMS,isomer #1	C[C@H](CC1=CC=CC=C1)N[Si](C)(C)C	1618.3	Standard polar	33892256
(R)-Amphetamine,2TMS,isomer #1	C[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	1539.5	Semi standard non polar	33892256
(R)-Amphetamine,2TMS,isomer #1	C[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	1524.0	Standard non polar	33892256
(R)-Amphetamine,2TMS,isomer #1	C[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	1644.4	Standard polar	33892256
(R)-Amphetamine,1TBDMS,isomer #1	C[C@H](CC1=CC=CC=C1)N[Si](C)(C)C(C)(C)C	1564.4	Semi standard non polar	33892256
(R)-Amphetamine,1TBDMS,isomer #1	C[C@H](CC1=CC=CC=C1)N[Si](C)(C)C(C)(C)C	1562.5	Standard non polar	33892256
(R)-Amphetamine,1TBDMS,isomer #1	C[C@H](CC1=CC=CC=C1)N[Si](C)(C)C(C)(C)C	1758.8	Standard polar	33892256
(R)-Amphetamine,2TBDMS,isomer #1	C[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1970.2	Semi standard non polar	33892256
(R)-Amphetamine,2TBDMS,isomer #1	C[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1936.9	Standard non polar	33892256
(R)-Amphetamine,2TBDMS,isomer #1	C[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1881.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Amphetamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9100000000-41224b447ebed58b4d86	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Amphetamine 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 - (R)-Amphetamine 10V, Positive-QTOF	splash10-00kr-0900000000-b3a524d7c495f48a74c3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Amphetamine 20V, Positive-QTOF	splash10-014r-1900000000-081ce3a25bbacda4ab98	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Amphetamine 40V, Positive-QTOF	splash10-0006-9300000000-5195de4351c8a02eb232	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Amphetamine 10V, Negative-QTOF	splash10-001i-0900000000-22cd79bae5466b52ae0a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Amphetamine 20V, Negative-QTOF	splash10-001i-1900000000-a4e4f7fb040e60f9e5ba	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Amphetamine 40V, Negative-QTOF	splash10-014l-4900000000-e652b091af97ea288b4c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Amphetamine 10V, Positive-QTOF	splash10-00kf-6900000000-4f5d22828acdcb13d83e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Amphetamine 20V, Positive-QTOF	splash10-0006-9000000000-c5766ace6b2031302336	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Amphetamine 40V, Positive-QTOF	splash10-0006-9000000000-c8535cbb285cac999590	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Amphetamine 10V, Negative-QTOF	splash10-0006-9200000000-0f66be3239e5e65d6028	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Amphetamine 20V, Negative-QTOF	splash10-0006-9100000000-6720c563d36a88e31cd6	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Amphetamine 40V, Negative-QTOF	splash10-002f-9000000000-f91f5b5177c2d32668fd	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Quadrupole Ion Trap, ESI+, Adduct: [M+H]+)	2022-02-11	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB028792

KNApSAcK ID

Not Available

Chemspider ID

30477

KEGG Compound ID

C07514

BioCyc ID

CPD-7659

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

32893

PDB ID

FRD

ChEBI ID

42724

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

Sulzer D, Sonders MS, Poulsen NW, Galli A: Mechanisms of neurotransmitter release by amphetamines: a review. Prog Neurobiol. 2005 Apr;75(6):406-33. [PubMed:15955613 ]
Chaudhry IA, Turkanis SA, Karler R: Characteristics of "reverse tolerance" to amphetamine-induced locomotor stimulation in mice. Neuropharmacology. 1988 Aug;27(8):777-81. [PubMed:3216957 ]
Leith NJ, Kuczenski R: Chronic amphetamine: tolerance and reverse tolerance reflect different behavioral actions of the drug. Pharmacol Biochem Behav. 1981 Sep;15(3):399-404. [PubMed:7291243 ]
Sax KW, Strakowski SM: Behavioral sensitization in humans. J Addict Dis. 2001;20(3):55-65. [PubMed:11681593 ]
Glennon RA, Yousif M, Patrick G: Stimulus properties of 1-(3,4-methylenedioxyphenyl)-2-aminopropane (MDA) analogs. Pharmacol Biochem Behav. 1988 Mar;29(3):443-9. [PubMed:2896360 ]

Showing metabocard for (R)-Amphetamine (HMDB0012128)

MOL for HMDB0012128 ((R)-Amphetamine)

3D MOL for HMDB0012128 ((R)-Amphetamine)

3D SDF for HMDB0012128 ((R)-Amphetamine)

3D-SDF for HMDB0012128 ((R)-Amphetamine)

PDB for HMDB0012128 ((R)-Amphetamine)

3D PDB for HMDB0012128 ((R)-Amphetamine)

SMILES for HMDB0012128 ((R)-Amphetamine)

INCHI for HMDB0012128 ((R)-Amphetamine)

Structure for HMDB0012128 ((R)-Amphetamine)

3D Structure for HMDB0012128 ((R)-Amphetamine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra