Metfendrazine (developmental code names HM-11, MO-482), also known as methphendrazine, is an irreversible and nonselective monoamine oxidase inhibitor (MAOI) of the hydrazine family.[1][2] It was investigated as an antidepressant, but was never marketed.
Chemistry
Metfendrazine, also known as methamphetamine hydrazide, is a phenethylamine, amphetamine, and hydrazine derivative.
It is an analogue and derivative of phenelzine (phenethylamine hydrazide) and pheniprazine (amphetamine hydrazide), as well as of phenethylamine, amphetamine, and methamphetamine.
References
- ^ Miquel J, Mijan CD (1962). "Metfendrazine, a new inhibitor of monoamine oxidase". Archivos del Instituto de Farmacología Experimental. 14. Madrid: 47–59.
- ^ Kothari NJ, Saunders JC, Kline NS, Griffen JA (October 1960). "A comparison of perphenazine, proketazine, nialamide and MO-482 in chronic schizophrenics". The American Journal of Psychiatry. 117 (4): 358–360. doi:10.1176/ajp.117.4.358. PMID 13753478.
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Non-specific | AAADTooltip Aromatic L-amino acid decarboxylase | |
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MAOTooltip Monoamine oxidase | |
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Phenethylamines (dopamine, epinephrine, norepinephrine) | PAHTooltip Phenylalanine hydroxylase | |
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THTooltip Tyrosine hydroxylase | |
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DBHTooltip Dopamine beta-hydroxylase | |
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PNMTTooltip Phenylethanolamine N-methyltransferase |
- Inhibitors: CGS-19281A
- SKF-64139
- SKF-7698
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COMTTooltip Catechol-O-methyl transferase | |
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Tryptamines (serotonin, melatonin) | TPHTooltip Tryptophan hydroxylase | |
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AANATTooltip Serotonin N-acetyl transferase | |
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ASMTTooltip Acetylserotonin O-methyltransferase | |
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Histamine | HDCTooltip Histidine decarboxylase | |
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HNMTTooltip Histamine N-methyltransferase |
- Substrates→Products: Histamine→N-Methylhistamine
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DAOTooltip Diamine oxidase |
- Substrates→Products: Histamine→Imidazole acetic acid
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See also: Receptor/signaling modulators • Adrenergics • Dopaminergics • Melatonergics • Serotonergics • Monoamine reuptake inhibitors • Monoamine releasing agents • Monoamine neurotoxins |
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Phenethylamines | |
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Amphetamines | |
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Phentermines | |
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Cathinones | |
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Phenylisobutylamines (and further-extended) | |
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Catecholamines (and close relatives) | |
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Cyclized phenethylamines | Phenylalkylpyrrolidines | |
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2-Benzylpiperidines (phenidates) | |
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Phenylmorpholines (phenmetrazines) | |
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Phenyloxazolamines (aminorexes) | |
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Isoquinolines and tetrahydroisoquinolines | |
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2-Aminoindanes | |
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2-Aminotetralins | |
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Others / unsorted |
- 1-Aminomethylindanes (e.g., 2CB-Ind, AMMI, bromojimscaline, jimscaline)
- 2-ADN
- 2-Benzhydrylpyrrolidine
- 2C-B-5-hemiFLY-α6 (BNAP)
- 3-Benzhydrylmorpholine
- 3-Phenylpiperidines (e.g., 3-phenylpiperidine, OSU-6162 (PNU-96391), LPH-5, LPH-48)
- 6-AB
- AL-1095
- Aminochromes (e.g., adrenochrome, adrenolutin)
- Benzazepines (e.g., fenoldopam, lorcaserin, SCHEMBL5334361)
- Benzocyclobutenes (e.g., 2CBCB-NBOMe, bromotomscaline, S33005, TCB-2, tomscaline)
- Benzoxepins (e.g., BBOX, IBOX, TFMBOX)
- Butyltolylquinuclidine
- Cypenamine (trans-2-phenylcyclopentylamine)
- Diphenidine
- Diphenylprolinol
- DMBMPP
- Ergolines (e.g., LSD)
- GYKI-52895
- HDMP-29
- Ivabradine
- Lumateperone and analogues (e.g., IHCH-7079, IHCH-7086, IHCH-7113, ITI-1549)
- Methoxphenidine
- Methylmorphenate
- Milnacipran
- MT-45
- 2-Naphthylamine
- Org 6582
- Partial ergolines (e.g., NDTDI, RU-27849, DEIMDHPCA, DEMPDHPCA, DEMPDHPCA-2C-D, RU-27251)
- PF-592,379
- Phenylcyclopropylamines (e.g., DMCPA, TMT, tranylcypromine)
- Tetrahydrobenzopyranylamines (e.g., CT-5126)
- Tricyclics (e.g., benzoctamine, dizocilpine)
- Z3517967757
- ZC-B
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Related compounds |
- 2-Furylethylamine
- 2-Pyrrolylethylamine
- 3-Pyrrolylethylamine
- 3-Pyrrolylpropylamine
- 2-Tetrahydrofurylethylamine
- 4-Benzylpiperidine
- 7-AB
- Alkylamines (e.g., 1,3-DMBATooltip 1,3-dimethylbutylamine, 1,4-DMAATooltip 1,4-dimethylamylamine, heptaminol, iproheptine, isometheptene, methylhexanamine/1,3-DMAA, octodrine, oenethyl, tuaminoheptane)
- Benzylamines (e.g., benzylamine, α-methylbenzylamine, MDM1EA, ALPHA, M-ALPHA, pargyline)
- Benzylpiperazines (e.g., benzylpiperazine, MDBZP, fipexide)
- Cyclohexylaminopropanes (e.g., propylhexedrine, norpropylhexedrine)
- Cyclopentylaminopropanes (e.g., isocyclamine, cyclopentamine)
- Phenoxyethylamines (e.g., 3,4,5-trimethoxyphenoxyethylamine, CT-4719, ORG-37684)
- Phenylalkenylamines (e.g., phenylbutenamine)
- Phenylalkynylamines (e.g., phenylbutynamine)
- Phenylpiperazines (e.g., 1-phenylpiperazine, mCPPTooltip meta-chlorophenylpiperazine, TFMPPTooltip trifluoromethylphenylpiperazine, oMPPTooltip ortho-methylphenylpiperazine, pFPPTooltip para-fluorophenylpiperazine, pMeOPPTooltip para-methoxyphenylpiperazine)
- Phenylpropylamines (e.g., phenylpropylamine, homo-MDA, homo-MDMA)
- Thienylaminopropanes (thiopropamines) (e.g., thiopropamine, methiopropamine, thiothinone)
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- See also: Tryptamines
- Ergolines and lysergamides
- Stimulants
- Entactogens
- Psychedelics
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