Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1036)
Drug Name
Metamfetamine
Synonyms
Metamfetamine; Metamfetaminum; Metamphetamine; Methyl-beta-phenylisopropylamine; Methylamphetamine; N-Methylamphetamine; Norodin; d-(S)-Methamphetamine; d-Deoxyephedrine; d-Desoxyephedrine; d-Methamphetamine; d-Methylamphetamine; D-1-Phenyl-2-methylaminopropane; Desyphed; L-Methamphetamine; METHAMPHETAMINE; d-N-Methylamphetamine; d-Phenylisopropylmethylamine; (+)-(S)-Deoxyephedrine; (+)-Methylamphetamine; (+)-N-Methylamphetamine; (S)-(+)-Deoxyephedrine; (S)-Methamphetamine; (S)-Methylamphetamine; 1-Phenyl-2-methylaminopropane
Indication Attention deficit hyperactivity disorder [ICD11: 6A05] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 149.23 Topological Polar Surface Area 12
Heavy Atom Count 11 Rotatable Bond Count 3
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 1
Cross-matching ID
PubChem CID
10836
PubChem SID
9373 ; 86393 ; 841176 ; 7979916 ; 8157860 ; 10318874 ; 15194699 ; 29229287 ; 46508541 ; 47217054 ; 47365454 ; 47515585 ; 47960002 ; 50004327 ; 53789276 ; 56311093 ; 56312330 ; 56313865 ; 56314133 ; 56314533 ; 57288565 ; 57326508 ; 76939162 ; 85239987 ; 96024877 ; 104234344 ; 104324404 ; 117516537 ; 128667762 ; 134337864 ; 134338686 ; 134977993 ; 136963523 ; 137001219 ; 142148255 ; 160964817 ; 164187274 ; 175268005 ; 175269473 ; 175443906 ; 178101505 ; 179252637 ; 184547219 ; 223856686 ; 226427302 ; 241092821 ; 250138934 ; 250231443
ChEBI ID
ChEBI:6809
CAS Number
537-46-2
TTD Drug ID
D0P6UB
Formula
C10H15N
Canonical SMILES
CC(CC1=CC=CC=C1)NC
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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Amphetamine DM003887
3007
Unclear - Unclear 1 [4] , [5] , [6]
p-Hydroxymethamphetamine DM006662
4655
Unclear - Unclear 1 [6] , [7]
Fenethylline Metabolite M-5( p-hydroxy-AP) DM000822
3651
Unclear - Unclear 2 [8]
Metamfetamine Metabolite M5 DM001359
7678
Unclear - Unclear 2 [8]
Norephedrine DM001363
26934
Unclear - Unclear 2 [8]
4-hydroxynorephedrine DM001362
6931150
Unclear - Unclear 3 [8]
Midostaurin Metabolite P6 DM001360
243
Unclear - Unclear 3 [8]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR009984 Metamfetamine Amphetamine Unclear - Unclear CYP2D6 [4], [5], [6]
MR009991 Metamfetamine p-hydroxymethamphetamine Unclear - Unclear CYP2D6 [6], [7]
MR009985 Amphetamine Metamfetamine Metabolite M5 Unclear - Unclear Unclear [8]
MR009987 Amphetamine Norephedrine Unclear - Unclear Unclear [8]
MR009989 Amphetamine 4-Hydroxyamphetamine Unclear - Unclear Unclear [8]
MR009992 P-hydroxymethamphetamine 4-Hydroxyamphetamine Unclear - Unclear Unclear [8]
MR009990 4-Hydroxyamphetamine 4-Hydroxynorephedrine Unclear - Unclear Unclear [8]
MR009986 Metamfetamine Metabolite M5 Benzoic acid Unclear - Unclear Unclear [8]
MR009988 Norephedrine 4-Hydroxynorephedrine Unclear - Unclear Unclear [8]
⏷ Show the Full List of 9 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Unclear metabolic mechanism (DME-unclear) DME1264 Enterococcus malodoratus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1278 Lactobacillus acetotolerans Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [3]
References
1 Metamfetamine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Cytochrome P450 2D6.1 and cytochrome P450 2D6.10 differ in catalytic activity for multiple substrates. Pharmacogenetics. 2001 Aug;11(6):477-87.
3 The demethylation of methamphetamine by intestinal microflora. J Pharm Pharmacol. 1973 May;25(5):422-4.
4 Sex- and dose-dependency in the pharmacokinetics and pharmacodynamics of (+)-methamphetamine and its metabolite (+)-amphetamine in rats
5 Drugs of abuse in a non-conventional sample; detection of methamphetamine and its main metabolite, amphetamine in abusers' clothes by HPLC with UV and fluorescence detection
6 Reduced CYP2D6 activity is a negative risk factor for methamphetamine dependence
7 Effects of methamphetamine and its primary human metabolite, p-hydroxymethamphetamine, on the development of the Australian blowfly Calliphora stygia
8 Metabolism of ( 14 C)methamphetamine in man, the guinea pig and the rat

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