Details of the Drug

General Information of Drug (ID: DMPM4SK)

Drug Name

Methamphetamine

Synonyms

METHAMPHETAMINE; Metamfetamine; d-Deoxyephedrine; d-Desoxyephedrine; d-Methamphetamine; d-N-Methylamphetamine; Metamphetamine; L-Methamphetamine; d-Methylamphetamine; Methylamphetamine; d-Phenylisopropylmethylamine; N-Methylamphetamine; (S)-Methamphetamine; Norodin; (+)-Methylamphetamine; d-(S)-Methamphetamine; D-1-Phenyl-2-methylaminopropane; Metamfetaminum; Desyphed; (+)-N-Methylamphetamine; (S)-Methylamphetamine; (+)-(S)-Deoxyephedrine; Methyl-beta-phenylisopropylamine; 1-Phenyl-2-methylaminopropane; (S)-(+)-Deoxyephedrine; Crank; Desohyephedrine; Metamfetamina; Meth; Methamphetaminum; Speed; Stimulex; Crank [Street Name]; Crystal Meth; Crystal Meth [Street Name]; Desyphed hydrochloride; ICE [Street Name]; Metamfetamine [INN];Metamfetaminum [Latin]; Metanfetamina [Spanish]; Methamphetaminum [JP]; Speed [Street Name]; D-Deoxyephedrine; D-Desoxyephedrine; D-Methamphetamine; D-Methylamphetamine; D-Phenylisopropylmethylamine;Desoxyn (TN); Metamfetamina [INN-Spanish]; Metamfetamine (INN); Metamfetamine-m; Metamfetaminum [INN-Latin]; Metanfetamina [INN-Spanish]; Meth (Street Name); Methamphetaminum [INN-Latin]; D-N-Methylamphetamine; D-(S)-Methamphetamine; D-N,alpha-dimethylphenethylamine; Methamphetamine, its salts, isomers, and salts of its isomers; N-Methyl-beta-phenylisopropylamin; N-Methyl-beta-phenylisopropylamin [German]; N-Methyl-beta-phenylisopropylamine; D-1-Phenyl-2-methylaminopropan; D-1-Phenyl-2-methylaminopropan [German]; S-(+)-Methamphetamine; D-N,alpha-Dimethylphenethylamine; N-Methyl-1-phenyl-2-propanamine; Benzeneethanamine, N,alpha-dimethyl-, (S)-(9CI); Benzeneethanamine, N,alpha-dimethyl-, (alphaS)-(9CI); Phenethylamine, N,alpha-dimethyl-, (S)-(+)-(8CI); (+)-(S)-N-alpha-Dimethylphenethylamine; (+)-2-(N-Methylamino)-1-phenylpropane; (+)-N,alpha-Dimethyl-beta-phenylethylamine; (+)-N,alpha-Dimethylphenethylamine; (+)-methamphetamine; (2S)-N-methyl-1-phenylpropan-2-amine; (S)-(+)-Methamphetamine; (S)-(+)-N,alpha,dimethylphenethylamine; (S)-N,alpha-Dimethylbenzeneethanamine; (S)-N,alpha-Dimethylbenzeneethanoamine; (alphaS)-N,alpha-dimethylbenzeneethanamine; 1-Phenyl-2-methylamino-propan; 1-Phenyl-2-methylamino-propan [German]; 2S-(+)-Methamphetamine; Methamfetamine

Indication

Disease Entry	ICD 11	Status	REF
Anxiety	N.A.	Approved	[1]
Attention deficit hyperactivity disorder	6A05.Z	Approved	[2]
Depression	6A70-6A7Z	Approved	[1]
Methamphetamine dependence	6C46.2	Approved	[1]
Obesity	5B81	Approved	[1]
Pain	MG30-MG3Z	Approved	[3]
Sexually transmitted infection	1A9Z	Approved	[1]
Substance dependence	N.A.	Approved	[1]
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Therapeutic Class

Central Nervous System Stimulants

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

149.23

Logarithm of the Partition Coefficient (xlogp)

2.1

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Bioavailability: 67% of drug becomes completely available to its intended biological destination(s) [4]
Clearance: The drug present in the plasma can be removed from the body at the rate of 4.4 mL/min/kg [5]
Elimination: 40% of drug is excreted from urine in the unchanged form [6]
Half-life: The concentration or amount of drug in body reduced by one-half in 4 - 5 hours [5]
Metabolism: The drug is metabolized via the hepatic []
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 1.9228 micromolar/kg/day [7]
Unbound Fraction: The unbound fraction of drug in plasma is 0.85% [5]
Vd: Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 4.3 L/kg [5]
Water Solubility: The ability of drug to dissolve in water is measured as 1000 mg/mL [6]

Adverse Drug Reaction (ADR)

ADR Term	Variation	Related DOT	DOT ID	REF
Schizophrenia	rs12591257	AGBL1	OT8NQLH0	[8]
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Chemical Identifiers

Formula: C10H15N
IUPAC Name: (2S)-N-methyl-1-phenylpropan-2-amine
Canonical SMILES: C[C@@H](CC1=CC=CC=C1)NC
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
InChIKey: MYWUZJCMWCOHBA-VIFPVBQESA-N

Cross-matching ID

PubChem CID: 10836
ChEBI ID: CHEBI:6809
CAS Number: 537-46-2
DrugBank ID: DB01577
TTD ID: D0P6UB
VARIDT ID: DR00256
INTEDE ID: DR1036
ACDINA ID: D00207

Combinatorial Drugs (CBD)

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Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Adrenergic receptor alpha-1B (ADRA1B)	TTBRKXS	ADA1B_HUMAN	Antagonist	[9]
Dopamine D2 receptor (D2R)	TTEX248	DRD2_HUMAN	Agonist	[3]

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Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Vesicular amine transporter 2 (SLC18A2)	DTT7VPB	VMAT2_HUMAN	Substrate	[10]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 2D6 (CYP2D6)_{Main DME}	DECB0K3	CP2D6_HUMAN	Substrate	[11]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-1 (PLCB1)	OT9HYT7A	PLCB1_HUMAN	Gene/Protein Processing	[12]
2-oxoglutarate dehydrogenase-like, mitochondrial (OGDHL)	OT1AZK6R	OGDHL_HUMAN	Gene/Protein Processing	[13]
3',5'-cyclic-AMP phosphodiesterase 4B (PDE4B)	OTOA8WU2	PDE4B_HUMAN	Drug Response	[14]
3',5'-cyclic-AMP phosphodiesterase 4D (PDE4D)	OT1RWFV0	PDE4D_HUMAN	Drug Response	[14]
5-hydroxytryptamine receptor 1A (HTR1A)	OT38K9MK	5HT1A_HUMAN	Drug Response	[15]
5-hydroxytryptamine receptor 6 (HTR6)	OT8GTDDY	5HT6R_HUMAN	Drug Response	[16]
Abnormal spindle-like microcephaly-associated protein (ASPM)	OTKXQMNA	ASPM_HUMAN	Gene/Protein Processing	[13]
Actin, alpha cardiac muscle 1 (ACTC1)	OTJU04B1	ACTC_HUMAN	Gene/Protein Processing	[13]
Activator of apoptosis harakiri (HRK)	OTR4GWJ0	HRK_HUMAN	Gene/Protein Processing	[13]
Acyloxyacyl hydrolase (AOAH)	OTOYBXKW	AOAH_HUMAN	Drug Response	[14]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Molecular Expression Atlas of This Drug

The Studied Disease

Anxiety

ICD Disease Classification

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Dopamine D2 receptor (D2R)	DTT	DRD2	2.50E-02	-0.08	-0.49
Vesicular amine transporter 2 (SLC18A2)	DTP	VMAT2	2.69E-02	-4.44E-02	-1.12E-01
Cytochrome P450 2D6 (CYP2D6)	DME	CYP2D6	7.30E-01	-1.91E-02	-1.41E-01

Molecular Expression Atlas (MEA)

MEA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Methamphetamine (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Tromethamine	DMOBLGK	Moderate	as urine pH determines the ionization state of weakly acidic or weakly alkaline drugs. Methamphetamine caused by Tromethamine mediated altered urine pH.	Acidosis [5C73]	[17]
Methylene blue	DMJAPE7	Major	Increased risk of hyperpyrexia by the combination of Methamphetamine and Methylene blue.	Acquired methaemoglobinaemia [3A93]	[18]
Dronedarone	DMA8FS5	Moderate	Decreased metabolism of Methamphetamine caused by Dronedarone mediated inhibition of CYP450 enzyme.	Angina pectoris [BA40]	[19]
Droxidopa	DM5YF4M	Moderate	Additive hypertensive effects by the combination of Methamphetamine and Droxidopa.	Autonomic nervous system disorder [8D87]	[20]
Esketamine	DMVU687	Major	Additive hypertensive effects by the combination of Methamphetamine and Esketamine.	Depression [6A70-6A7Z]	[21]
SODIUM CITRATE	DMHPD2Y	Moderate	as urine pH determines the ionization state of weakly acidic or weakly alkaline drugs. Methamphetamine caused by SODIUM CITRATE mediated altered urine pH.	Discovery agent [N.A.]	[17]
Mirabegron	DMS1GYT	Moderate	Decreased metabolism of Methamphetamine caused by Mirabegron mediated inhibition of CYP450 enzyme.	Functional bladder disorder [GC50]	[22]
Cobicistat	DM6L4H2	Moderate	Decreased metabolism of Methamphetamine caused by Cobicistat mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[23]
Sodium acetate anhydrous	DMH21E0	Moderate	as urine pH determines the ionization state of weakly acidic or weakly alkaline drugs. Methamphetamine caused by Sodium acetate anhydrous mediated altered urine pH.	Hypo-osmolality/hyponatraemia [5C72]	[17]
Givosiran	DM5PFIJ	Moderate	Decreased metabolism of Methamphetamine caused by Givosiran mediated inhibition of CYP450 enzyme.	Inborn porphyrin/heme metabolism error [5C58]	[24]
Berotralstat	DMWA2DZ	Moderate	Decreased metabolism of Methamphetamine caused by Berotralstat mediated inhibition of CYP450 enzyme.	Innate/adaptive immunodeficiency [4A00]	[25]
Polyethylene glycol	DM4I1JP	Moderate	Increased risk of lowers seizure threshold by the combination of Methamphetamine and Polyethylene glycol.	Irritable bowel syndrome [DD91]	[26]
Glycerol phenylbutyrate	DMDGRQO	Moderate	Decreased metabolism of Methamphetamine caused by Glycerol phenylbutyrate mediated inhibition of CYP450 enzyme.	Liver disease [DB90-DB9Z]	[27]
Dacomitinib	DMOH8VY	Moderate	Decreased metabolism of Methamphetamine caused by Dacomitinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[28]
Vemurafenib	DM62UG5	Moderate	Decreased metabolism of Methamphetamine caused by Vemurafenib mediated inhibition of CYP450 enzyme.	Melanoma [2C30]	[29]
Panobinostat	DM58WKG	Moderate	Decreased metabolism of Methamphetamine caused by Panobinostat mediated inhibition of CYP450 enzyme.	Multiple myeloma [2A83]	[30]
Ozanimod	DMT6AM2	Moderate	Increased risk of hyperpyrexia by the combination of Methamphetamine and Ozanimod.	Multiple sclerosis [8A40]	[31]
Fedratinib	DM4ZBK6	Moderate	Decreased metabolism of Methamphetamine caused by Fedratinib mediated inhibition of CYP450 enzyme.	Myeloproliferative neoplasm [2A20]	[32]
Nilotinib	DM7HXWT	Moderate	Decreased metabolism of Methamphetamine caused by Nilotinib mediated inhibition of CYP450 enzyme.	Myeloproliferative neoplasm [2A20]	[33]
Rolapitant	DM8XP26	Moderate	Decreased metabolism of Methamphetamine caused by Rolapitant mediated inhibition of CYP450 enzyme.	Nausea/vomiting [MD90]	[34]
Safinamide	DM0YWJC	Moderate	Decreased metabolism of Methamphetamine caused by Safinamide mediated inhibition of non-CYP450 enzyme.	Parkinsonism [8A00]	[35]
ABIRATERONE	DM8V75C	Moderate	Decreased metabolism of Methamphetamine caused by ABIRATERONE mediated inhibition of CYP450 enzyme.	Prostate cancer [2C82]	[34]
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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Aminobenzoate sodium	E00435	517441	Lubricant
Stearic acid	E00079	5281	Emulsifying agent; Solubilizing agent; Viscosity-controlling agent; lubricant
Beta-D-lactose	E00099	6134	Diluent; Dry powder inhaler carrier; Lyophilization aid
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant
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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Methamphetamine 5 mg tablet	5 mg	Oral Tablet	Oral

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References

1	Methamphetamine FDA Label
2	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 4803).
3	Pharmacotherapy for obesity. Drugs. 2005;65(10):1391-418.
4	Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
5	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
6	BDDCS applied to over 900 drugs
7	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
8	Evidence for shared genetic risk between methamphetamine-induced psychosis and schizophrenia. Neuropsychopharmacology. 2013 Sep;38(10):1864-70. doi: 10.1038/npp.2013.94. Epub 2013 Apr 12.
9	Mirtazapine treatment after conditioning with methamphetamine alters subsequent expression of place preference. Drug Alcohol Depend. 2009 Jan 1;99(1-3):231-9.
10	Synthesis and Discovery of Arylpiperidinylquinazolines: New Inhibitors of the Vesicular Monoamine Transporter. J Med Chem. 2018 Oct 25;61(20):9121-9131.
11	Cytochrome P450 2D6.1 and cytochrome P450 2D6.10 differ in catalytic activity for multiple substrates. Pharmacogenetics. 2001 Aug;11(6):477-87.
12	Inhibition of PLC1 signaling pathway regulates methamphetamine self-administration and neurotoxicity in rats. Food Chem Toxicol. 2021 Mar;149:111970. doi: 10.1016/j.fct.2021.111970. Epub 2021 Jan 7.
13	Methamphetamine alters the normal progression by inducing cell cycle arrest in astrocytes. PLoS One. 2014 Oct 7;9(10):e109603.
14	Genome-wide association for methamphetamine dependence: convergent results from 2 samples. Arch Gen Psychiatry. 2008 Mar;65(3):345-55. doi: 10.1001/archpsyc.65.3.345.
15	Serotonin 1A receptor gene is associated with Japanese methamphetamine-induced psychosis patients. Neuropharmacology. 2010 Feb;58(2):452-6. doi: 10.1016/j.neuropharm.2009.09.006. Epub 2009 Sep 10.
16	Serotonin 6 receptor gene is associated with methamphetamine-induced psychosis in a Japanese population. Drug Alcohol Depend. 2011 Jan 1;113(1):1-7. doi: 10.1016/j.drugalcdep.2010.06.021. Epub 2010 Aug 11.
17	Anggard E, Jonsson LE, Hogmark AL, Gunne LM "Amphetamine metabolism in amphetamine psychosis." Clin Pharmacol Ther 14 (1973): 870-80. [PMID: 4729903]
18	Boakes AJ, Laurence DR, Teoh PC, Barar FS, Benedikter LT, Pritchard BN "Interactions between sympathomimetic amines and antidepressant agents in man." Br Med J 1 (1973): 311-5. [PMID: 4685619]
19	Product Information. Ambien (zolpidem). sanofi-aventis, Bridgewater, NJ.
20	Product Information. Northera (droxidopa). Chelsea Therapeutics Inc, Charlotte, NC.
21	Product Information. Spravato (esketamine). Janssen Pharmaceuticals, Titusville, NJ.
22	Product Information. Myrbetriq (mirabegron). Astellas Pharma US, Inc, Deerfield, IL.
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24	Product Information. Givlaari (givosiran). Alnylam Pharmaceuticals, Cambridge, MA.
25	Product Information. Orladeyo (berotralstat). BioCryst Pharmaceuticals Inc, Durham, NC.
26	Product Information. Suprep Bowel Prep Kit (magnesium/potassium/sodium sulfates). Braintree Laboratories, Braintree, MA.
27	Cerner Multum, Inc. "UK Summary of Product Characteristics.".
28	Product Information. Vizimpro (dacomitinib). Pfizer U.S. Pharmaceuticals Group, New York, NY.
29	Product Information. Zelboraf (vemurafenib). Genentech, South San Francisco, CA.
30	Cerner Multum, Inc. "Australian Product Information.".
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33	Product Information. Tasigna (nilotinib). Novartis Pharmaceuticals, East Hanover, NJ.
34	Product Information. Fycompa (perampanel). Eisai Inc, Teaneck, NJ.
35	Cusson JR, Goldenberg E, Larochelle P "Effect of a novel monoamine-oxidase inhibitor, moclobemide on the sensitivity to intravenous tyramine and norepinephrine in humans." J Clin Pharmacol 31 (1991): 462-7. [PMID: 2050833]