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Showing toxin card for Methamphetamine (T3D3052)

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Version 1.0
Creation Date 2009-07-21 20:28:53
Update Date 2010-05-18 21:01:54
Accession Number T3D3052
Name Methamphetamine
Compound Type
  • Adrenergic Agent
  • Adrenergic Uptake Inhibitor
  • Central Nervous System Stimulant
  • Dopamine Agent
  • Dopamine Uptake Inhibitor
  • Drug
  • Sympathomimetic
Description Methamphetamine is a psychostimulant and sympathomimetic drug. It is a member of the amphetamine group of sympathomimetic amines and is a scheduled drug in most countries.
Synonyms
  1. (+ )-methylamphetamine
  2. (+)-(s)-deoxyephedrine
  3. (+)-(s)-n-alpha-dimethylphenethylamine
  4. (+)-2-(N-Methylamino)-1-phenylpropane
  5. (+)-methamphetamine
  6. (+)-methylamphetamine
  7. (+)-n,alpha-dimethyl-beta-phenylethylamine
  8. (+)-n,alpha-dimethylphenethylamine
  9. (+)-n-methylamphetamine
  10. (2S)-N-methyl-1-phenylpropan-2-amine
  11. (s)-(+)-deoxyephedrine
  12. (s)-(+)-methamphetamine
  13. (s)-(+)-n,alpha,dimethylphenethylamine
  14. (s)-methamphetamine
  15. (s)-methylamphetamine
  16. (s)-n,alpha-dimethylbenzeneethanamine
  17. (s)-n,alpha-dimethylbenzeneethanoamine
  18. 1-Phenyl-2-methylamino-propan [German]
  19. 1-Phenyl-2-methylaminopropane
  20. 2S-(+)-Methamphetamine
  21. D-(s)-methamphetamine
  22. d-1-Phenyl-2-methylaminopropan [German]
  23. D-1-Phenyl-2-methylaminopropane
  24. D-deoxyephedrine
  25. D-desoxyephedrine
  26. D-methamphetamine
  27. D-methylamphetamine
  28. D-n,alpha-dimethylphenethylamine
  29. D-n-methylamphetamine
  30. D-phenylisopropylmethylamine
  31. Desoxyephedrine hydrochloride
  32. L-methamphetamine
  33. Ice
  34. Metamfetamina [inn-spanish]
  35. Metamfetaminum [inn-latin]
  36. Metamphetamine
  37. Metanfetamina [inn-spanish]
  38. Meth
  39. Methamphetaminum [inn-latin]
  40. Methyl-beta-phenylisopropylamine
  41. Methylamphetamine
  42. N-Methyl-1-phenyl-2-propanamine
  43. N-methyl-beta-phenylisopropylamin [german]
  44. N-methyl-beta-phenylisopropylamine
  45. N-methylamphetamine
  46. S-(+)-methamphetamine
Chemical IUPAC Name methyl(1-phenylpropan-2-yl)amine
Chemical Formula C10H15N
Chemical Structure Structure
CAS Registry Number 537-46-2
InChI Identifier InChI=1S/C10H15N/c1-9(11-2)8-10-6-4-3-5-7-10/h3-7,9,11H,8H2,1-2H3
InChI Key InChIKey=MYWUZJCMWCOHBA-UHFFFAOYSA-N
PubChem Compound ID 10836 Link Image
KEGG ID C07164 Link Image
UniProt ID Not Available
OMIM ID Not Available
ChEBI ID 6809 Link Image
BioCyc ID Not Available
SuperToxic ID Not Available
CTD ID Not Available
Stitch ID Methamphetamine Link Image
DrugBank ID DB01577 Link Image
PDB ID Not Available
ACToR ID Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Methamphetamine Link Image
Monoisotopic Mass 149.120449
MOL File Show
PDB File Show
SDF File Show
SMILES CNC(C)CC1=CC=CC=C1
Appearance Not Available
Melting Point Not Available
Solubility Not Available
Predicted LogP 2.2368
Route of Exposure Oral
Mechanism of Action Methamphetamine enters the brain and triggers a cascading release of norepinephrine, dopamine and serotonin. To a lesser extent methamphetamine acts as a dopaminergic and adrenergic reuptake inhibitor and in high concentrations as a monamine oxidase inhibitor (MAOI). The mechanism of action involved in producing the beneficial behavioral changes seen in hyperkinetic children receiving methamphetamine is unknown.
Metabolism Hepatic. The primary site of metabolism is in the liver by aromatic hydroxylation, N-dealkylation and deamination. At least seven metabolites have been identified in the urine.
Toxicity Values Not Available
Lethal Dose Not Available
Carcinogenicity (IARC Classification) Not Available
Uses/Sources Not Available
Minimum Risk Level Not Available
Health Effects Using large amounts of these drugs can result in a condition known as amphetamine psychosis -- which can result in auditory, visual and tactile hallucinations, intense paranoia, irrational thoughts and beliefs, delusions, and mental confusion.
Symptoms Manifestations of acute overdosage with methamphetamine include restlessness, tremor, hyperreflexia, rapid respiration, confusion, assaultiveness, hallucinations, panic states, hyperpyrexia, and rhabdomyolysis. Fatigue and depression usually follow the central stimulation. Cardiovascular effects include arrhythmias, hypertension or hypotension, and circulatory collapse. Gastrointestinal symptoms include nausea, vomiting, diarrhea, and abdominal cramps. Fatal poisoning usually terminates in convulsions and coma.
Treatment Management of acute methamphetamine intoxication is largely symptomatic and includes gastric evacuation, administration of activated charcoal, and sedation. Experience with hemodialysis or peritoneal dialysis is inadequate to permit recommendations in this regard. Acidification of urine increases methamphetamine excretion, but is believed to increase risk of acute renal failure if myoglobinuria is present. Intravenous phentolamine has been suggested for possible acute, severe hypertension, if this complicates methamphetamine overdosage. Usually a gradual drop in blood pressure will result when sufficient sedation has been achieved. Chlorpromazine has been reported to be useful in decreasing CNS stimulation and sympathomimetic effects. (V650)
General References
  • V255 - McGregor C, Srisurapanont M, Jittiwutikarn J, Laobhripatr S, Wongtan T, White JM: The nature, time course and severity of methamphetamine withdrawal. Addiction. 2005 Sep;100(9):1320-9. [PubMed Link Image]
  • V258 - Shaner JW: Caries associated with methamphetamine abuse. J Mich Dent Assoc. 2002 Sep;84(9):42-7. [PubMed Link Image]
  • V254 - Schepers RJ, Oyler JM, Joseph RE Jr, Cone EJ, Moolchan ET, Huestis MA: Methamphetamine and amphetamine pharmacokinetics in oral fluid and plasma after controlled oral methamphetamine administration to human volunteers. Clin Chem. 2003 Jan;49(1):121-32. [PubMed Link Image]
  • V257 - Hasan AA, Ciancio S: Relationship between amphetamine ingestion and gingival enlargement. Pediatr Dent. 2004 Sep-Oct;26(5):396-400. [PubMed Link Image]
  • V256 - Bennett BA, Hollingsworth CK, Martin RS, Harp JJ: Methamphetamine-induced alterations in dopamine transporter function. Brain Res. 1998 Jan 26;782(1-2):219-27. [PubMed Link Image]
Targets
  1. Alpha-1A adrenergic receptor
  2. Alpha-1B adrenergic receptor
Target 1 [top]
Target 1 ID 1142
Target 1 Name Alpha-1A adrenergic receptor
Target 1 Mechanism of Action Methamphetamine enters the brain and triggers a cascading release of norepinephrine, dopamine and serotonin. To a lesser extent methamphetamine acts as a dopaminergic and adrenergic reuptake inhibitor and in high concentrations as a monamine oxidase inhibitor (MAOI). The mechanism of action involved in producing the beneficial behavioral changes seen in hyperkinetic children receiving methamphetamine is unknown.
Target 1 Description 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
Target 1 Synonyms
  1. Alpha 1A-adrenoreceptor; Alpha 1A-adrenoceptor; Alpha-1C adrenergic receptor; Alpha-adrenergic receptor 1c
Target 1 Gene Name ADRA1A
Target 1 Protein Sequence >Alpha-1A adrenergic receptor 
MVFLSGNASDSSNCTQPPAPVNISKAILLGVILGGLILFGVLGNILVILSVACHRHLHSV
THYYIVNLAVADLLLTSTVLPFSAIFEVLGYWAFGRVFCNIWAAVDVLCCTASIMGLCII
SIDRYIGVSYPLRYPTIVTQRRGLMALLCVWALSLVISIGPLFGWRQPAPEDETICQINE
EPGYVLFSALGSFYLPLAIILVMYCRVYVVAKRESRGLKSGLKTDKSDSEQVTLRIHRKN
APAGGSGMASAKTKTHFSVRLLKFSREKKAAKTLGIVVGCFVLCWLPFFLVMPIGSFFPD
FKPSETVFKIVFWLGYLNSCINPIIYPCSSQEFKKAFQNVLRIQCLCRKQSSKHALGYTL
HPPSQAVEGQHKDMVRIPVGSRETFYRISKTDGVCEWKFFSSMPRGSARITVSKDQSSCT
TARVRSKSFLQVCCCVGPSTPSLDKNHQVPTIKVHTISLSENGEEV
Target 1 Number of Residues 466
Target 1 Molecular Weight 51486.0
Target 1 Theoretical pI 9.23
Target 1 GO Classification
Function
amine receptor activity
adrenoceptor activity
alpha-adrenergic receptor activity
alpha1-adrenergic receptor activity
signal transducer activity
receptor activity
transmembrane receptor activity
G-protein coupled receptor activity
rhodopsin-like receptor activity
Process
cellular process
cell communication
signal transduction
cell surface receptor linked signal transduction
G-protein coupled receptor protein signaling pathway
Component
cell
membrane
intrinsic to membrane
integral to membrane
Target 1 General Function Involved in alpha1-adrenergic receptor activity
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • 28-51
  • 65-88
  • 100-122
  • 144-167
  • 182-205
  • 274-297
  • 306-329
Target 1 Essentiality Non Essential
Target 1 Domain Function PF00001:7tm_1
Target 1 GenBank ID Protein Not Available
Target 1 UniProtKB ID P35348 Link Image
Target 1 Cellular Location Cell membrane
Target 1 Gene Sequence >1401 bp 
ATGGTGTTTCTCTCGGGAAATGCTTCCGACAGCTCCAACTGCACCCAACCGCCGGCACCG
GTGAACATTTCCAAGGCCATTCTGCTCGGGGTGATCTTGGGGGGCCTCATTCTTTTCGGG
GTGCTGGGTAACATCCTAGTGATCCTCTCCGTAGCCTGTCACCGACACCTGCACTCAGTC
ACGCACTACTACATCGTCAACCTGGCGGTGGCCGACCTCCTGCTCACCTCCACGGTGCTG
CCCTTCTCCGCCATCTTCGAGGTCCTAGGCTACTGGGCCTTCGGCAGGGTCTTCTGCAAC
ATCTGGGCGGCAGTGGATGTGCTGTGCTGCACCGCGTCCATCATGGGCCTCTGCATCATC
TCCATCGACCGCTACATCGGCGTGAGCTACCCGCTGCGCTACCCAACCATCGTCACCCAG
AGGAGGGGTCTCATGGCTCTGCTCTGCGTCTGGGCACTCTCCCTGGTCATATCCATTGGA
CCCCTGTTCGGCTGGAGGCAGCCGGCCCCCGAGGACGAGACCATCTGCCAGATCAACGAG
GAGCCGGGCTACGTGCTCTTCTCAGCGCTGGGCTCCTTCTACCTGCCTCTGGCCATCATC
CTGGTCATGTACTGCCGCGTCTACGTGGTGGCCAAGAGGGAGAGCCGGGGCCTCAAGTCT
GGCCTCAAGACCGACAAGTCGGACTCGGAGCAAGTGACGCTCCGCATCCATCGGAAAAAC
GCCCCGGCAGGAGGCAGCGGGATGGCCAGCGCCAAGACCAAGACGCACTTCTCAGTGAGG
CTCCTCAAGTTCTCCCGGGAGAAGAAAGCGGCCAAAACGCTGGGCATCGTGGTCGGCTGC
TTCGTCCTCTGCTGGCTGCCTTTTTTCTTAGTCATGCCCATTGGGTCTTTCTTCCCTGAT
TTCAAGCCCTCTGAAACAGTTTTTAAAATAGTATTTTGGCTCGGATATCTAAACAGCTGC
ATCAACCCCATCATATACCCATGCTCCAGCCAAGAGTTCAAAAAGGCCTTTCAGAATGTC
TTGAGAATCCAGTGTCTCCGCAGAAAGCAGTCTTCCAAACATGCCCTGGGCTACACCCTG
CACCCGCCCAGCCAGGCCGTGGAAGGGCAACACAAGGACATGGTGCGCATCCCCGTGGGA
TCAAGAGAGACCTTCTACAGGATCTCCAAGACGGATGGCGTTTGTGAATGGAAATTTTTC
TCTTCCATGCCCCGTGGATCTGCCAGGATTACAGTGTCCAAAGACCAATCCTCCTGTACC
ACAGCCCGGGTGAGAAGTAAAAGCTTTTTGGAGGTCTGCTGCTGTGTAGGGCCCTCAACC
CCCAGCCTTGACAAGAACCATCAAGTTCCAACCATTAAGGTCCACACCATCTCCCTCAGT
GAGAACGGGGAGGAAGTCTAG
Target 1 GenBank Gene ID Not Available
Target 1 GeneCard ID ADRA1A Link Image
Target 1 GenAtlas ID ADRA1A Link Image
Target 1 HGNC ID HGNC:277 Link Image
Target 1 Chromosome Location Not Available
Target 1 Locus 8p21-p11.2
Target 1 SNPs SNPJam Report Link Image
Target 1 Toxin References
  • S912 - 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 Link Image]
  • S911 - Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]
Target 1 General References 8396931; 8024574; 8183249; 8564208; 7815325; 7737411; 9490024; 10493934
Target 2 [top]
Target 2 ID 1193
Target 2 Name Alpha-1B adrenergic receptor
Target 2 Mechanism of Action Methamphetamine enters the brain and triggers a cascading release of norepinephrine, dopamine and serotonin. To a lesser extent methamphetamine acts as a dopaminergic and adrenergic reuptake inhibitor and in high concentrations as a monamine oxidase inhibitor (MAOI). The mechanism of action involved in producing the beneficial behavioral changes seen in hyperkinetic children receiving methamphetamine is unknown.
Target 2 Description This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system
Target 2 Synonyms
  1. Alpha 1B-adrenoreceptor; Alpha 1B-adrenoceptor
Target 2 Gene Name ADRA1B
Target 2 Protein Sequence >Alpha-1B adrenergic receptor 
MNPDLDTGHNTSAPAHWGELKNANFTGPNQTSSNSTLPQLDITRAISVGLVLGAFILFAI
VGNILVILSVACNRHLRTPTNYFIVNLAMADLLLSFTVLPFSAALEVLGYWVLGRIFCDI
WAAVDVLCCTASILSLCAISIDRYIGVRYSLQYPTLVTRRKAILALLSVWVLSTVISIGP
LLGWKEPAPNDDKECGVTEEPFYALFSSLGSFYIPLAVILVMYCRVYIVAKRTTKNLEAG
VMKEMSNSKELTLRIHSKNFHEDTLSSTKAKGHNPRSSIAVKLFKFSREKKAAKTLGIVV
GMFILCWLPFFIALPLGSLFSTLKPPDAVFKVVFWLGYFNSCLNPIIYPCSSKEFKRAFV
RILGCQCRGRGRRRRRRRRRLGGCAYTYRPWTRGGSLERSQSRKDSLDDSGSCLSGSQRT
LPSASPSPGYLGRGAPPPVELCAFPEWKAPGALLSLPAPEPPGRRGRHDSGPLFTFKLLT
EPESPGTDGGASNGGCEAAADVANGQPGFKSNMPLAPGQF
Target 2 Number of Residues 520
Target 2 Molecular Weight 56835.4
Target 2 Theoretical pI 9.79
Target 2 GO Classification
Function
amine receptor activity
adrenoceptor activity
alpha-adrenergic receptor activity
alpha1-adrenergic receptor activity
signal transducer activity
receptor activity
transmembrane receptor activity
G-protein coupled receptor activity
rhodopsin-like receptor activity
Process
cellular process
cell communication
signal transduction
cell surface receptor linked signal transduction
G-protein coupled receptor protein signaling pathway
Component
cell
membrane
intrinsic to membrane
integral to membrane
Target 2 General Function Involved in alpha1-adrenergic receptor activity
Target 2 Pathways Not Available
Target 2 Reactions Not Available
Target 2 Signals
  • None
Target 2 Transmembrane Regions
  • 46-70
  • 84-105
  • 116-141
  • 162-184
  • 202-224
  • 296-319
  • 327-351
Target 2 Essentiality Non Essential
Target 2 Domain Function PF00001:7tm_1
Target 2 GenBank ID Protein Not Available
Target 2 UniProtKB ID P35368 Link Image
Target 2 Cellular Location Cell membrane
Target 2 Gene Sequence >1563 bp 
ATGAATCCCGACCTGGACACCGGCCACAACACATCAGCACCTGCCCACTGGGGAGAGTTG
AAAAATGCCAACTTCACTGGCCCCAACCAGACCTCGAGCAACTCCACACTGCCCCAGCTG
GACATCACCAGGGCCATCTCTGTGGGCCTGGTGCTGGGCGCCTTCATCCTCTTTGCCATC
GTGGGCAACATCCTAGTCATCTTGTCTGTGGCCTGCAACCGGCACCTGCGGACGCCCACC
AACTACTTCATTGTCAACCTGGCCATGGCCGACCTGCTGTTGAGCTTCACCGTCCTGCCC
TTCTCAGCGGCCCTAGAGGTGCTCGGCTACTGGGTGCTGGGGCGGATCTTCTGTGACATC
TGGGCAGCCGTGGATGTCCTGTGCTGCACAGCGTCCATTCTGAGCCTGTGCGCCATCTCC
ATCGATCGCTACATCGGGGTGCGCTACTCTCTGCAGTATCCCACGCTGGTCACCCGGAGG
AAGGCCATCTTGGCGCTGCTCAGTGTCTGGGTCTTGTCCACCGTCATCTCCATCGGGCCT
CTCCTTGGGTGGAAGGAGCCGGCACCCAACGATGACAAGGAGTGCGGGGTCACCGAAGAA
CCCTTCTATGCCCTCTTCTCCTCTCTGGGCTCCTTCTACATCCCTCTGGCGGTCATTCTA
GTCATGTACTGCCGTGTCTATATAGTGGCCAAGAGAACCACCAAGAACCTAGAGGCAGGA
GTCATGAAGGAGATGTCCAACTCCAAGGAGCTGACCCTGAGGATCCATTCCAAGAACTTT
CACGAGGACACCCTTAGCAGTACCAAGGCCAAGGGCCACAACCCCAGGAGTTCCATAGCT
GTCAAACTTTTTAAGTTCTCCAGGGAAAAGAAAGCAGCTAAGACGTTGGGCATTGTGGTC
GGTATGTTCATCTTGTGCTGGCTACCCTTCTTCATCGCTCTACCGCTTGGCTCCTTGTTC
TCCACCCTGAAGCCCCCCGACGCCGTGTTCAAGGTGGTGTTCTGGCTGGGCTACTTCAAC
AGCTGCCTCAACCCCATCATCTACCCATGCTCCAGCAAGGAGTTCAAGCGCGCTTTCGTG
CGCATCCTCGGGTGCCAGTGCCGCGGCCGCGGCCGCCGCCGACGCCGCCGCCGCCGTCGC
CTGGGCGGCTGCGCCTACACCTACCGGCCGTGGACGCGCGGCGGCTCGCTGGAGCGCTCG
CAGTCGCGCAAGGACTCGCTGGACGACAGCGGCAGCTGCCTGAGCGGCAGCCAGCGGACC
CTGCCCTCGGCCTCGCCGAGCCCGGGCTACCTGGGCCGCGGCGCGCCACCGCCAGTCGAG
CTGTGCGCCTTCCCCGAGTGGAAGGCGCCCGGCGCCCTCCTGAGCCTGCCCGCGCCTGAG
CCCCCCGGCCGCCGCGGCCGCCACGACTCGGGCCCGCTCTTCACCTTCAAGCTCCTGACC
GAGCCCGAGAGCCCCGGGACCGACGGCGGCGCCAGCAACGGAGGCTGCGAGGCCGCGGCC
GACGTGGCCAACGGGCAGCCGGGCTTCAAAAGCAACATGCCCCTGGCGCCCGGGCAGTTT
TAG
Target 2 GenBank Gene ID Not Available
Target 2 GeneCard ID ADRA1B Link Image
Target 2 GenAtlas ID ADRA1B Link Image
Target 2 HGNC ID HGNC:278 Link Image
Target 2 Chromosome Location Not Available
Target 2 Locus 5q23-q32
Target 2 SNPs SNPJam Report Link Image
Target 2 Toxin References
  • S912 - 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 Link Image]
  • S911 - Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]
  • V259 - Battaglia G, Fornai F, Busceti CL, Lembo G, Nicoletti F, De Blasi A: Alpha-1B adrenergic receptor knockout mice are protected against methamphetamine toxicity. J Neurochem. 2003 Jul;86(2):413-21. [PubMed Link Image]
Target 2 General References 1328250; 8183249; 7815325

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