(R)Methyl-(1-methyl-2-phenyl-ethyl)-amine

ID: ALA1201201

Chembl Id: CHEMBL1201201

Cas Number: 537-46-2

PubChem CID: 10836

Max Phase: Approved

First Approval: 1943

Molecular Formula: C10H15N

Molecular Weight: 149.24

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: (s)-phenylmethylaminopropane | Metamfetamine | Methamphetamine | J6.362B | NSC-25115 | METHAMPHETAMINE|Metamfetamine|d-Deoxyephedrine|d-Desoxyephedrine|d-Methamphetamine|Methylamphetamine|d-N-Methylamphetamine|Metamphetamine|d-Methylamphetamine|N-Methylamphetamine|d-Phenylisopropylmethylamine|(S)-Methamphetamine|D-1-Phenyl-2-methylaminopropane|Norodin|(S)-Methylamphetamine|(+)-Methylamphetamine|d-(S)-Methamphetamine|Metamfetamina|Metamfetaminum|Methyl-beta-phenylisopropylamine|(+)-N-MethylamphetShow More

Synonyms from Alternative Forms(9): Methylamfetamine hydrochloride | Methamphetamine hydrochloride | Desoxyephedrine hydrochloride | Metamfetamine hydrochloride | Methamphetamine hcl | NSC-169505 | Desoxyn | Methampex | Methamphetamine hydrochloride cii

Canonical SMILES:  CN[C@@H](C)Cc1ccccc1

Standard InChI:  InChI=1S/C10H15N/c1-9(11-2)8-10-6-4-3-5-7-10/h3-7,9,11H,8H2,1-2H3/t9-/m0/s1

Standard InChI Key:  MYWUZJCMWCOHBA-VIFPVBQESA-N

Alternative Forms

  1. Alternative Forms:

  2. Parent:

    ALA1201201

    METHAMPHETAMINE

Associated Targets(Human)

SIGMAR1 Tclin Sigma opioid receptor (6358 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TAAR1 Tclin Trace amine-associated receptor 1 (1397 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Liver microsomes (16955 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC22A5 Tbio Solute carrier family 22 member 5 (138 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Whole blood (398 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CISD1 Tchem CDGSH iron-sulfur domain-containing protein 1 (222 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Homo sapiens (32628 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Rattus norvegicus (775804 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAOB Monoamine oxidase B (894 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Maob Monoamine oxidase B (2209 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TAAR1 Trace amine-associated receptor 1 (20 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Taar1 Trace amine-associated receptor 1 (899 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Taar1 Trace amine-associated receptor 1 (1619 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Slc22a5 Solute carrier family 22 member 5 (44 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Slc22a3 Solute carrier family 22 member 3 (35 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Slc18a2 Synaptic vesicular amine transporter (631 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SARS-CoV-2 (38078 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: YesOral: YesChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: Yes
Chirality: YesAvailability: YesProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 149.24Molecular Weight (Monoisotopic): 149.1204AlogP: 1.84#Rotatable Bonds: 3
Polar Surface Area: 12.03Molecular Species: BASEHBA: 1HBD: 1
#RO5 Violations: HBA (Lipinski): 1HBD (Lipinski): 1#RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: 10.21CX LogP: 2.24CX LogD: -0.44
Aromatic Rings: 1Heavy Atoms: 11QED Weighted: 0.69Np Likeness Score: -0.21

References

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3. Chu DT, Nordeen CW, Hardy DJ, Swanson RN, Giardina WJ, Pernet AG, Plattner JJ..  (1991)  Synthesis, antibacterial activities, and pharmacological properties of enantiomers of temafloxacin hydrochloride.,  34  (1): [PMID:1846917] [10.1021/jm00105a025]
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5. Obach RS, Lombardo F, Waters NJ..  (2008)  Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.,  36  (7): [PMID:18426954] [10.1124/dmd.108.020479]
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8. Lewin AH, Miller GM, Gilmour B..  (2011)  Trace amine-associated receptor 1 is a stereoselective binding site for compounds in the amphetamine class.,  19  (23): [PMID:22037049] [10.1016/j.bmc.2011.10.007]
9. Sakatis MZ, Reese MJ, Harrell AW, Taylor MA, Baines IA, Chen L, Bloomer JC, Yang EY, Ellens HM, Ambroso JL, Lovatt CA, Ayrton AD, Clarke SE..  (2012)  Preclinical strategy to reduce clinical hepatotoxicity using in vitro bioactivation data for >200 compounds.,  25  (10): [PMID:22931300] [10.1021/tx300075j]
10. Wu X, Huang W, Prasad PD, Seth P, Rajan DP, Leibach FH, Chen J, Conway SJ, Ganapathy V..  (1999)  Functional characteristics and tissue distribution pattern of organic cation transporter 2 (OCTN2), an organic cation/carnitine transporter.,  290  (1): [PMID:10454528]
11. Wu X, Prasad PD, Leibach FH, Ganapathy V..  (1998)  cDNA sequence, transport function, and genomic organization of human OCTN2, a new member of the organic cation transporter family.,  246  (1): [PMID:9618255] [10.1006/bbrc.1998.8669]
12. Wu X, Kekuda R, Huang W, Fei YJ, Leibach FH, Chen J, Conway SJ, Ganapathy V..  (1998)  Identity of the organic cation transporter OCT3 as the extraneuronal monoamine transporter (uptake2) and evidence for the expression of the transporter in the brain.,  273  (1): [PMID:9830022] [10.1074/jbc.273.49.32776]
13. Noorizadeh H, Noorizadeh M, Farmany A.  (2012)  Advanced QSRR models of toxicological screening of basic drugs in whole blood by UPLC-TOFMS,  21  (12): [10.1007/s00044-012-9977-1]
14. Ding D, Nickell JR, Deaciuc AG, Penthala NR, Dwoskin LP, Crooks PA..  (2013)  Synthesis and evaluation of novel azetidine analogs as potent inhibitors of vesicular [3H]dopamine uptake.,  21  (21): [PMID:23993667] [10.1016/j.bmc.2013.08.001]
15. Unpublished dataset, 
16. Settimo L, Bellman K, Knegtel RM..  (2013)  Comparison of the accuracy of experimental and predicted pKa values of basic and acidic compounds.,  [PMID:24249037] [10.1007/s11095-013-1232-z]
17. Reese EA, Norimatsu Y, Grandy MS, Suchland KL, Bunzow JR, Grandy DK..  (2014)  Exploring the determinants of trace amine-associated receptor 1's functional selectivity for the stereoisomers of amphetamine and methamphetamine.,  57  (2): [PMID:24354319] [10.1021/jm401316v]
18. Ding D, Nickell JR, Dwoskin LP, Crooks PA..  (2015)  Quinolyl analogues of norlobelane: novel potent inhibitors of [(3)H]dihydrotetrabenazine binding and [(3)H]dopamine uptake at the vesicular monoamine transporter-2.,  25  (13): [PMID:25991431] [10.1016/j.bmcl.2015.04.105]
19. WHO Anatomical Therapeutic Chemical Classification, 
20. Geldenhuys WJ, Yonutas HM, Morris DL, Sullivan PG, Darvesh AS, Leeper TC..  (2016)  Identification of small molecules that bind to the mitochondrial protein mitoNEET.,  26  (21): [PMID:27687671] [10.1016/j.bmcl.2016.09.009]
21. Glennon RA..  (2017)  The 2014 Philip S. Portoghese Medicinal Chemistry Lectureship: The "Phenylalkylaminome" with a Focus on Selected Drugs of Abuse.,  60  (7): [PMID:28244748] [10.1021/acs.jmedchem.7b00085]
22. Chen M, Suzuki A, Thakkar S, Yu K, Hu C, Tong W..  (2016)  DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans.,  21  (4): [PMID:26948801] [10.1016/j.drudis.2016.02.015]
23. Unpublished dataset, 
24. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]