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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (6)transporters (1) Show 7 proteins XML

enzymes (6)transporters (1) Show 7 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:00 UTC

HMDB ID

HMDB0015516

Secondary Accession Numbers

HMDB15516

Metabolite Identification

Common Name

Dextroamphetamine

Description

Dextroamphetamine is only found in individuals that have used or taken this drug. It is the dextrorotary stereoisomer of the amphetamine molecule, which can take two different forms. It is a slightly polar, weak base and is lipophilic. The exact mechanism of action is not known. Dextroamphetamine stimulates the release of norepinephrine from central adrenergic receptors. At higher dosages, it causes release of dopamine from the mesocorticolimbic system and the nigrostriatal dopamine systems by reversal of the monoamine transporters. Dextroamphetamine may also act as a direct agonist on central 5-HT receptors and may inhibit monoamine oxidase (MAO). In the periphery, amphetamines are believed to cause the release of noradrenaline by acting on the adrenergic nerve terminals and alpha- and beta-receptors. Modulation of serotonergic pathways may contribute to the calming affect.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(+)-(S)-Amphetamine	ChEBI
(+)-alpha-Methylphenethylamine	ChEBI
(+)-alpha-Methylphenylethylamine	ChEBI
(+)-Amphetamine	ChEBI
(AlphaS)-alpha-methylbenzeneethanamine	ChEBI
(S)-(+)-Amphetamine	ChEBI
(S)-(+)-beta-Phenylisopropylamine	ChEBI
(S)-1-Phenyl-2-aminopropane	ChEBI
(S)-1-Phenyl-2-propylamine	ChEBI
(S)-alpha-Methylbenzeneethanamine	ChEBI
D-Amphetamine	ChEBI
Dexamphetamine	ChEBI
Dexamfetamine	Kegg
(+)-a-Methylphenethylamine	Generator
(+)-Α-methylphenethylamine	Generator
(+)-a-Methylphenylethylamine	Generator
(+)-Α-methylphenylethylamine	Generator
(AlphaS)-a-methylbenzeneethanamine	Generator
(AlphaS)-α-methylbenzeneethanamine	Generator
(S)-(+)-b-Phenylisopropylamine	Generator
(S)-(+)-Β-phenylisopropylamine	Generator
(S)-a-Methylbenzeneethanamine	Generator
(S)-Α-methylbenzeneethanamine	Generator
(S)-Amphetamine	HMDB
Celltech brand OF dextroamphetamine sulfate	HMDB
Oxydess	HMDB
Sulfate, dextroamphetamine	HMDB
D Amphetamine	HMDB
Curban	HMDB
Dextro-amphetamine sulfate	HMDB
GlaxoSmithKline brand OF dextroamphetamine sulfate	HMDB
Dextro-amphetamine	HMDB
Dextro amphetamine sulfate	HMDB
DextroStat	HMDB
Shire brand OF dextroamphetamine sulfate	HMDB
D-Amphetamine sulfate	HMDB
Dexedrine	HMDB
Dextroamphetamine sulfate	HMDB
Mallinckrodt brand OF dextroamphetamine sulfate	HMDB
Pasadena brand OF dextroamphetamine	HMDB
Vortech brand OF dextroamphetamine sulfate	HMDB
D Amphetamine sulfate	HMDB
Dextro amphetamine	HMDB
Dextroamphetamine	ChEBI

Chemical Formula

C₉H₁₃N

Average Molecular Weight

135.2062

Monoisotopic Molecular Weight

135.104799421

IUPAC Name

(2S)-1-phenylpropan-2-amine

Traditional Name

amphetamine

CAS Registry Number

51-64-9

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-/m0/s1

InChI Key

KWTSXDURSIMDCE-QMMMGPOBSA-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:4469 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Biofluid or Excreta

Excreta

Urine (PMID: 21059682)

Non-excretory biofluid

Blood (PMID: 21059682)

Process

Not Available

Role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	< 25 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.74 g/L	Not Available
LogP	1.76	SANGSTER (1994); similar isomer

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	16.08 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]+	129.672	31661259
DarkChem	[M-H]-	127.071	31661259
DeepCCS	[M+H]+	133.152	30932474
DeepCCS	[M-H]-	129.938	30932474
DeepCCS	[M-2H]-	166.909	30932474
DeepCCS	[M+Na]+	142.447	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 Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dextroamphetamine	C[C@H](N)CC1=CC=CC=C1	1645.8	Standard polar	33892256
Dextroamphetamine	C[C@H](N)CC1=CC=CC=C1	1128.0	Standard non polar	33892256
Dextroamphetamine	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
Dextroamphetamine,1TMS,isomer #1	C[C@@H](CC1=CC=CC=C1)N[Si](C)(C)C	1334.7	Semi standard non polar	33892256
Dextroamphetamine,1TMS,isomer #1	C[C@@H](CC1=CC=CC=C1)N[Si](C)(C)C	1339.0	Standard non polar	33892256
Dextroamphetamine,1TMS,isomer #1	C[C@@H](CC1=CC=CC=C1)N[Si](C)(C)C	1618.3	Standard polar	33892256
Dextroamphetamine,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
Dextroamphetamine,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
Dextroamphetamine,2TMS,isomer #1	C[C@@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	1644.4	Standard polar	33892256
Dextroamphetamine,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
Dextroamphetamine,1TBDMS,isomer #1	C[C@@H](CC1=CC=CC=C1)N[Si](C)(C)C(C)(C)C	1562.5	Standard non polar	33892256
Dextroamphetamine,1TBDMS,isomer #1	C[C@@H](CC1=CC=CC=C1)N[Si](C)(C)C(C)(C)C	1758.8	Standard polar	33892256
Dextroamphetamine,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
Dextroamphetamine,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
Dextroamphetamine,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 - Dextroamphetamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9100000000-41224b447ebed58b4d86	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dextroamphetamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-f40d32a5bced4783345a	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dextroamphetamine 35V, Positive-QTOF	splash10-0006-9000000000-6e32961bde8922a0f2f3	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextroamphetamine 10V, Positive-QTOF	splash10-00kr-0900000000-e842cf90085d664ef1c3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextroamphetamine 20V, Positive-QTOF	splash10-014r-2900000000-2b5fda1ab431107344f5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextroamphetamine 40V, Positive-QTOF	splash10-0fr6-9400000000-b1a9d46f37313e323a64	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextroamphetamine 10V, Negative-QTOF	splash10-001i-1900000000-0e421d19515a1429b103	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextroamphetamine 20V, Negative-QTOF	splash10-001i-1900000000-fff6e7346b2c36a8ab21	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextroamphetamine 40V, Negative-QTOF	splash10-014l-7900000000-3cd62c7239479d83b257	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextroamphetamine 10V, Positive-QTOF	splash10-00kf-6900000000-4f5d22828acdcb13d83e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextroamphetamine 20V, Positive-QTOF	splash10-0006-9000000000-c5766ace6b2031302336	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextroamphetamine 40V, Positive-QTOF	splash10-0006-9000000000-c8535cbb285cac999590	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextroamphetamine 10V, Negative-QTOF	splash10-0006-9200000000-0f66be3239e5e65d6028	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextroamphetamine 20V, Negative-QTOF	splash10-0006-9100000000-6720c563d36a88e31cd6	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextroamphetamine 40V, Negative-QTOF	splash10-002f-9000000000-f91f5b5177c2d32668fd	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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 DB01576	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01576	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

DB01576

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5621

KEGG Compound ID

C07884

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dextroamphetamine

METLIN ID

Not Available

PubChem Compound

5826

PDB ID

Not Available

ChEBI ID

4469

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

Warneke L: Psychostimulants in psychiatry. Can J Psychiatry. 1990 Feb;35(1):3-10. [PubMed:2180548 ]
Yamada H, Baba T, Hirata Y, Oguri K, Yoshimura H: Studies on N-demethylation of methamphetamine by liver microsomes of guinea-pigs and rats: the role of flavin-containing mono-oxygenase and cytochrome P-450 systems. Xenobiotica. 1984 Nov;14(11):861-6. [PubMed:6506758 ]
Wagner GJ, Rabkin R: Effects of dextroamphetamine on depression and fatigue in men with HIV: a double-blind, placebo-controlled trial. J Clin Psychiatry. 2000 Jun;61(6):436-40. [PubMed:10901342 ]
Butefisch CM, Davis BC, Sawaki L, Waldvogel D, Classen J, Kopylev L, Cohen LG: Modulation of use-dependent plasticity by d-amphetamine. Ann Neurol. 2002 Jan;51(1):59-68. [PubMed:11782985 ]
Martinsson L, Yang X, Beck O, Wahlgren NG, Eksborg S: Pharmacokinetics of dexamphetamine in acute stroke. Clin Neuropharmacol. 2003 Sep-Oct;26(5):270-6. [PubMed:14520168 ]
Greer CA, Alpern HP: Maturational changes related to dopamine in the effects of d-amphetamine, cocaine, nicotine, and strychnine on seizure susceptibility. Psychopharmacology (Berl). 1979 Sep;64(3):255-60. [PubMed:116267 ]
Lile JA, Stoops WW, Durell TM, Glaser PE, Rush CR: Discriminative-stimulus, self-reported, performance, and cardiovascular effects of atomoxetine in methylphenidate-trained humans. Exp Clin Psychopharmacol. 2006 May;14(2):136-47. [PubMed:16756417 ]
Patel JB, Migler B: A sensitive and selective monkey conflict test. Pharmacol Biochem Behav. 1982 Oct;17(4):645-9. [PubMed:7178177 ]
Chiueh CC, Moore KE: D-amphetamine-induced release of "newly synthesized" and "stored" dopamine from the caudate nucleus in vivo. J Pharmacol Exp Ther. 1975 Mar;192(3):642-53. [PubMed:1120962 ]
Glick SD, Cox RD, Greenstein S: Relationship of rats' spatial preferences to effects of d-amphetamine on timing behavior. Eur J Pharmacol. 1975 Aug;33(1):173-82. [PubMed:1236804 ]

Enzymes

Enzyme Details

1. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

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

2. Synaptic vesicular amine transporter

General function:: Involved in transmembrane transport
Specific function:: Involved in the ATP-dependent vesicular transport of biogenic amine neurotransmitters. Pumps cytosolic monoamines including dopamine, norepinephrine, serotonin, and histamine into synaptic vesicles. Requisite for vesicular amine storage prior to secretion via exocytosis
Gene Name:: SLC18A2
Uniprot ID:: Q05940
Molecular weight:: 55712.1

References

Sulzer D, Chen TK, Lau YY, Kristensen H, Rayport S, Ewing A: Amphetamine redistributes dopamine from synaptic vesicles to the cytosol and promotes reverse transport. J Neurosci. 1995 May;15(5 Pt 2):4102-8. [PubMed:7751968 ]
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 ]

Enzyme Details

3. Sodium-dependent dopamine transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:: SLC6A3
Uniprot ID:: Q01959
Molecular weight:: 68494.255

References

Zhen J, Chen N, Reith ME: Differences in interactions with the dopamine transporter as revealed by diminishment of Na(+) gradient and membrane potential: dopamine versus other substrates. Neuropharmacology. 2005 Nov;49(6):769-79. Epub 2005 Aug 24. [PubMed:16122767 ]
Kuczenski R, Segal DS, Cho AK, Melega W: Hippocampus norepinephrine, caudate dopamine and serotonin, and behavioral responses to the stereoisomers of amphetamine and methamphetamine. J Neurosci. 1995 Feb;15(2):1308-17. [PubMed:7869099 ]
Rothman RB, Dersch CM, Ananthan S, Partilla JS: Studies of the biogenic amine transporters. 13. Identification of "agonist" and "antagonist" allosteric modulators of amphetamine-induced dopamine release. J Pharmacol Exp Ther. 2009 May;329(2):718-28. doi: 10.1124/jpet.108.149088. Epub 2009 Feb 24. [PubMed:19244097 ]

Enzyme Details

4. Alpha-1A adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins
Gene Name:: ADRA1A
Uniprot ID:: P35348
Molecular weight:: 51486.0

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Enzyme Details

5. Alpha-1B adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system
Gene Name:: ADRA1B
Uniprot ID:: P35368
Molecular weight:: 56835.4

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

6. Trace amine-associated receptor 1

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Receptor for trace amines, including beta- phenylethylamine (b-PEA), p-tyramine (p-TYR), octopamine and tryptamine, with highest affinity for b-PEA and p-TYR. Unresponsive to classical biogenic amines, such as epinephrine and histamine and only partially activated by dopamine and serotonine. Trace amines are biogenic amines present in very low levels in mammalian tissues. Although some trace amines have clearly defined roles as neurotransmitters in invertebrates, the extent to which they function as true neurotransmitters in vertebrates has remained speculative. Trace amines are likely to be involved in a variety of physiological functions that have yet to be fully understood. The signal transduced by this receptor is mediated by the G(s)-class of G-proteins which activate adenylate cyclase
Gene Name:: TAAR1
Uniprot ID:: Q96RJ0
Molecular weight:: 39091.3

References

Reese EA, Bunzow JR, Arttamangkul S, Sonders MS, Grandy DK: Trace amine-associated receptor 1 displays species-dependent stereoselectivity for isomers of methamphetamine, amphetamine, and para-hydroxyamphetamine. J Pharmacol Exp Ther. 2007 Apr;321(1):178-86. Epub 2007 Jan 11. [PubMed:17218486 ]
Xie Z, Westmoreland SV, Bahn ME, Chen GL, Yang H, Vallender EJ, Yao WD, Madras BK, Miller GM: Rhesus monkey trace amine-associated receptor 1 signaling: enhancement by monoamine transporters and attenuation by the D2 autoreceptor in vitro. J Pharmacol Exp Ther. 2007 Apr;321(1):116-27. Epub 2007 Jan 18. [PubMed:17234900 ]
Wolinsky TD, Swanson CJ, Smith KE, Zhong H, Borowsky B, Seeman P, Branchek T, Gerald CP: The Trace Amine 1 receptor knockout mouse: an animal model with relevance to schizophrenia. Genes Brain Behav. 2007 Oct;6(7):628-39. Epub 2006 Dec 21. [PubMed:17212650 ]
Xie Z, Miller GM: Trace amine-associated receptor 1 is a modulator of the dopamine transporter. J Pharmacol Exp Ther. 2007 Apr;321(1):128-36. Epub 2007 Jan 18. [PubMed:17234899 ]
Miller GM, Verrico CD, Jassen A, Konar M, Yang H, Panas H, Bahn M, Johnson R, Madras BK: Primate trace amine receptor 1 modulation by the dopamine transporter. J Pharmacol Exp Ther. 2005 Jun;313(3):983-94. Epub 2005 Mar 11. [PubMed:15764732 ]

Transporters

Enzyme Details

1. Sodium-dependent noradrenaline transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:: SLC6A2
Uniprot ID:: P23975
Molecular weight:: 69331.42

References

Dlugos A, Freitag C, Hohoff C, McDonald J, Cook EH, Deckert J, de Wit H: Norepinephrine transporter gene variation modulates acute response to D-amphetamine. Biol Psychiatry. 2007 Jun 1;61(11):1296-305. Epub 2007 Jan 17. [PubMed:17239355 ]
Dlugos AM, Hamidovic A, Palmer AA, de Wit H: Further evidence of association between amphetamine response and SLC6A2 gene variants. Psychopharmacology (Berl). 2009 Oct;206(3):501-11. doi: 10.1007/s00213-009-1628-y. [PubMed:19727679 ]
Burnette WB, Bailey MD, Kukoyi S, Blakely RD, Trowbridge CG, Justice JB Jr: Human norepinephrine transporter kinetics using rotating disk electrode voltammetry. Anal Chem. 1996 Sep 1;68(17):2932-8. [PubMed:8794928 ]

Showing metabocard for Dextroamphetamine (HMDB0015516)

MOL for HMDB0015516 (Dextroamphetamine)

3D MOL for HMDB0015516 (Dextroamphetamine)

3D SDF for HMDB0015516 (Dextroamphetamine)

3D-SDF for HMDB0015516 (Dextroamphetamine)

PDB for HMDB0015516 (Dextroamphetamine)

3D PDB for HMDB0015516 (Dextroamphetamine)

SMILES for HMDB0015516 (Dextroamphetamine)

INCHI for HMDB0015516 (Dextroamphetamine)

Structure for HMDB0015516 (Dextroamphetamine)

3D Structure for HMDB0015516 (Dextroamphetamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References

References

References

References

References

Transporters

References