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Metfendrazine

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From Wikipedia, the free encyclopedia

Chemical compound

Pharmaceutical compound

Metfendrazine
Clinical data

Other names	Methphendrazine; HM-11; MO-482;N-Aminomethamphetamine; Methamphetamine hydrazide;N-Amino-N-methylamphetamine
Routes of administration	Oral
ATC code	none
Legal status
Legal status	In general: uncontrolled
Identifiers
IUPAC name 1-methyl-1-(1-methyl-2-phenyl-ethyl)hydrazine
CAS Number	3734-26-7^Y
PubChemCID	19516
ChemSpider	18390
UNII	A52QTC656T
CompTox Dashboard(EPA)	DTXSID701257364
Chemical and physical data
Formula	C₁₀H₁₆N₂
Molar mass	164.252 g·mol⁻¹

Metfendrazine (developmental code namesHM-11,MO-482), also known asmethphendrazine, is anirreversible andnonselective monoamine oxidase inhibitor (MAOI) of thehydrazine family.^[1]^[2] It was investigated as anantidepressant, but was never marketed.

Chemistry

[edit]

Metfendrazine, also known as methamphetamine hydrazide, is aphenethylamine,amphetamine, andhydrazine derivative.

It is ananalogue and derivative ofphenelzine (phenethylamine hydrazide) andpheniprazine (amphetamine hydrazide), as well as ofphenethylamine,amphetamine, andmethamphetamine.

References

[edit]

^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.

Monoamine metabolism modulators

Non-specific

AAADTooltip Aromatic L-amino acid decarboxylase

Substrates→Products:L-DOPA (levodopa)→Dopamine
5-HTP→Serotonin
L-Histidine→Histamine
Phenylalanine→Phenethylamine
L-Tyrosine→Tyramine
Tryptophan→Tryptamine

MAOTooltip Monoamine oxidase

Substrates→Products (with ALDHTooltip Aldehyde dehydrogenase/ALRTooltip ALR):Epinephrine (adrenaline)→DHMA Metanephrine→MHPG/VMA Norepinephrine (noradrenaline)→DHMA Normetanephrine→MHPG/VMA Dopamine→DOPAC 3-Methoxytyramine→HVA Serotonin→5-HIAA Inhibitors:Non-selective:Benmoxin Caroxazone Echinopsidine Furazolidone Guineesine Hydralazine Indantadol Iproclozide Iproniazid Isocarboxazid Isoniazid Linezolid Mebanazine Metfendrazine Nialamide Octamoxin Paraxazone Phenelzine Pheniprazine Phenoxypropazine Pivhydrazine Procarbazine Safrazine Tranylcypromine
Inhibitors:MAO-A-selective:Amiflamine Bazinaprine Befloxatone Brofaromine Cimoxatone Clorgiline CX157 (Tyrima) Eprobemide Esuprone Harmala alkaloids (e.g.,harmine,harmaline,harman,norharman,tetrahydroharmine) Methylene blue Metralindole Minaprine Moclobemide Pirlindole Sercloremine Tetrindole Toloxatone
Inhibitors:MAO-B selective:Adarigiline Almoxatone D-Deprenyl Desmethylselegiline Ethanol Ladostigil Lazabemide Milacemide Mofegiline Nicotine Pargyline^‡ Rasagiline Safinamide Selegiline (L-Deprenyl) Sembragiline Tisolagiline Vafidemstat

Phenethylamines
(dopamine,epinephrine,
norepinephrine)

PAHTooltip Phenylalanine hydroxylase	Substrates→Products:Phenylalanine→Tyrosine Inhibitors:3,4-Dihydroxystyrene α-Methylphenylalanine
THTooltip Tyrosine hydroxylase	Substrates→Products:Tyrosine→L-DOPA (levodopa) Inhibitors:2-Hydroxyestradiol 2-Hydroxyestrone 3-Iodotyrosine α-Methyl-5-hydroxytryptophan (α-Me-5-HTP) α-Methylphenylalanine Aquayamycin Bulbocapnine Methyldopa (α-methyl-L-DOPA) Metirosine (α-methyl-p-tyrosine) Oudenone
DBHTooltip Dopamine beta-hydroxylase	Substrates→Products:Dopamine→Norepinephrine (Noradrenaline) Inhibitors:Bupicomide Disulfiram Dopastin Etamicastat Fusaric acid Nepicastat Phenopicolinic acid Tropolone Zamicastat
PNMTTooltip Phenylethanolamine N-methyltransferase	Substrates→Products:Norepinephrine (noradrenaline)→Epinephrine (adrenaline) Inhibitors:CGS-19281A SKF-64139 SKF-7698
COMTTooltip Catechol-O-methyl transferase	Substrates→Products:Dopamine→3-Methoxytyramine DOPAC→Homovanillic acid Norepinephrine→Normetanephrine Epinephrine→Metanephrine DOPEG→MOPEG DOMA→VMA 2-Hydroxyestradiol→2-Methoxyestradiol 2-Hydroxyestrone→2-Methoxyestrone 4-Hydroxyestradiol→4-Methoxyestradiol 4-Hydroxyestrone→4-Methoxyestrone Inhibitors:2-Hydroxyestradiol 2-Hydroxyestrone Entacapone Nebicapone Neluxicapone Nitecapone Opicapone Quinalizarin Tolcapone

Tryptamines
(serotonin,melatonin)

TPHTooltip Tryptophan hydroxylase	Substrates→Products:Tryptophan→5-HTP Inhibitors:AGN-2979 Fenclonine (PCPA) Telotristat ethyl
AANATTooltip Serotonin N-acetyl transferase	Substrates→Products:Serotonin→N-Acetylserotonin
ASMTTooltip Acetylserotonin O-methyltransferase	Substrates→Products:N-Acetylserotonin→Melatonin

Histamine

HDCTooltip Histidine decarboxylase	Substrates→Products:L-Histidine→Histamine Inhibitors:Catechin Alpha-Fluoromethylhistidine Histidine methyl ester Meciadanol Naringenin Tritoqualine
HNMTTooltip Histamine N-methyltransferase	Substrates→Products:Histamine→N-Methylhistamine Inhibitors:Amodiaquine Diphenhydramine Harmaline Metoprine Quinacrine SKF-91488 Tacrine
DAOTooltip Diamine oxidase	Substrates→Products:Histamine→Imidazole acetic acid Inhibitors:Pimagedine (aminoguanidine)

See also:Receptor/signaling modulators •Adrenergics •Dopaminergics •Melatonergics •Serotonergics •Monoamine reuptake inhibitors •Monoamine releasing agents •Monoamine neurotoxins

v t e Hydrazines
4-PTSC Acylhydrazine ADH Adjudin Agaritine Benmoxin Cadralazine Carbazide Carbidopa Carbohydrazide Daminozide Dihydralazine DNPH Endralazine Gyromitrin HBT Hydralazine Hydrazide Hydrazine Hydrazone Iproclozide Iproniazid Isocarboxazid Isoniazid Mebanazine Metfendrazine MMH Nialamide Octamoxin PEH Phenelzine Pheniprazine Phenoxypropazine Phenylhydrazine Pildralazine Pimagedine Pivalylbenzhydrazine Procarbazine Safrazine Semicarbazide Semicarbazone SDMH Tetrafluorohydrazine UDMH

Hydrazines

v t e Phenethylamines
Phenethylamines	Psychedelics:25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iBu 2C-iP 2C-N 2C-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-tBu 2C-TFE 2C-TFM 2C-YN 2C-V Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants:Phenylethanolamine Hordenine Phenethylamine Phenpromethamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens:Lophophine MDPEA MDMPEA Others:Biscaline BOH Buscaline DMPEA
Amphetamines	Psychedelics:3C-AL 3C-BZ 3C-E 3C-MAL 3C-P Aleph Beatrice Bromo-DragonFLY D-Deprenyl DMA DMCPA DMMDA DOB DOC DOEF DOET DOI DOM DON DOPR DOTFM Ganesha MMDA MMDA-2 Psi-DOM TMA TeMA ZDCM-04 Stimulants:2-FA 2-FMA 3-FA 3-FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine,Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine,Levofenfluramine) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine,Levomethamphetamine) Methoxyphenamine MMA Morforex Norfenfluramine L-Norpseudoephedrine N,alpha-Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PCA PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens:4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 6-Chloro-MDMA 6-EAPB 6-IT 6-MAPB 6-MAPDB EDA IAP 2,3-MDA 3,4-MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others:3,4-DCA Amiflamine DiFMDA Selegiline (alsoD-Deprenyl)
Phentermines	Stimulants:Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens:MDPH MDMPH Others:Cericlamine
Cathinones	Stimulants:3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB N-Ethylhexedrone N-Ethylpentedrone Pentedrone Pentylone Radafaxine Entactogens:3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone Propylone
Phenylisobutylamines	Entactogens:4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants:Phenylisobutylamine
Phenylalkylpyrrolidines	Stimulants:α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
Catecholamines (and close relatives)	6-FNE 6-OHDA a-Me-DA a-Me-TRA Adrenochrome Ciladopa D-DOPA (Dextrodopa) Dimetofrine Dopamine Epinephrine Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L-DOPA (Levodopa) L-DOPS (Droxidopa) L-Phenylalanine L-Tyrosine m-Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N,N-Dimethyldopamine Nordefrin (Levonordefrin) Norepinephrine Norfenefrine (m-Octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine
Miscellaneous	AL-LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Ephenidine Etafedrine ETH-LAD Famprofazone Fluorolintane Hexapradol IP-LAD Lysergic acid amide Lysergic acid 2-butyl amide Lysergic acid 2,4-dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT-45 PARGY-LAD Phenibut PRO-LAD Pronethalol Salbutamol (Levosalbutamol) Solriamfetol Theodrenaline Thiamphenicol UWA-101 Venlafaxine

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