Chlorphentermine

Chlorphentermine
Clinical data
Routes of; administration	Oral, Insufflated, Rectal
ATC code	A08AA (WHO)
Legal status
Legal status	CA: Schedule IV; UK: Class C; US: Schedule III;
Pharmacokinetic data
Biological half-life	40 hours
Excretion	Renal
Identifiers
	IUPAC name 1-(4-chlorophenyl)-2-methylpropan-2-amine;
Synonyms	p-Chloro-α,α-dimethylphenethylamine
CAS Number	461-78-9 151-06-4
PubChem (CID)	10007
DrugBank	DB01556
ChemSpider	9613
UNII	NHW07912O7
KEGG	C07559
ChEMBL	CHEMBL1201269
ECHA InfoCard	100.006.651
Chemical and physical data
Formula	C10H14ClN
Molar mass	183.68 g/mol
3D model (Jmol)	Interactive image
	SMILES Clc1ccc(cc1)CC(N)(C)C ;
	InChI InChI=1S/C10H14ClN/c1-10(2,12)7-8-3-5-9(11)6-4-8/h3-6H,7,12H2,1-2H3 ; Key:ZCKAMNXUHHNZLN-UHFFFAOYSA-N ;
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Chlorphentermine (trade names Apsedon, Desopimon, Lucofen) is a serotonergic appetite suppressant of the amphetamine family. Developed in 1962, it is the 4-chloro derivative of the better known appetite suppressant phentermine,^[1] which is still in current use.

Chlorphentermine acts as a highly selective serotonin releasing agent (SRA).^[2] It is not a psychostimulant and has little or no abuse potential, but is classed as a Schedule III drug in the USA due mainly to its similarity to other appetite suppressants such as diethylpropion which have been more widely abused. It is no longer used due mainly to safety concerns, as it has a serotonergic effects profile similar to other withdrawn appetite suppressants such as fenfluramine and aminorex which were found to cause pulmonary hypertension and cardiac fibrosis following prolonged use.^[3]

The plasma half-life is about five days.^[4] It was withdrawn from the market in the UK in 1974.^[4]

References[edit]

^ Gylys JA, Hart JJ, Warren MR. Chlorphentermine, a new anorectic agent. Journal of Pharmacology and Experimental Therapeutics. 1962 Sep;137:365-73.
^ Rothman RB, Baumann MH, Dersch CM, Romero DV, Rice KC, Carroll FI, et al. (2001). "Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin.". Synapse. 39 (1): 32–41. doi:10.1002/1098-2396(20010101)39:1<32::AID-SYN5>3.0.CO;2-3. PMID 11071707.
^ Rothman RB, Ayestas MA, Dersch CM, Baumann MH. Aminorex, fenfluramine, and chlorphentermine are serotonin transporter substrates. Implications for primary pulmonary hypertension. Circulation. 1999 Aug 24;100(8):869-75.
^ ^a ^b Craddock, D (1976). "Anorectic drugs: use in general practice.". Drugs. 11 (5): 378–93. PMID 782835.

[1] Gylys JA, Hart JJ, Warren MR. Chlorphentermine, a new anorectic agent. Journal of Pharmacology and Experimental Therapeutics. 1962 Sep;137:365-73.

[pmid11071707-2] Rothman RB, Baumann MH, Dersch CM, Romero DV, Rice KC, Carroll FI, et al. (2001). "Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin.". Synapse. 39 (1): 32–41. doi:10.1002/1098-2396(20010101)39:1<32::AID-SYN5>3.0.CO;2-3. PMID 11071707.

[3] Rothman RB, Ayestas MA, Dersch CM, Baumann MH. Aminorex, fenfluramine, and chlorphentermine are serotonin transporter substrates. Implications for primary pulmonary hypertension. Circulation. 1999 Aug 24;100(8):869-75.

[1976rev-4] Craddock, D (1976). "Anorectic drugs: use in general practice.". Drugs. 11 (5): 378–93. PMID 782835.

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v t e Phenethylamines

Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-AN 2C-B-FLY βk-2C-B 2C-C 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-I 2C-N 2C-P 2C-SE 2C-T 2C-T-2 2C-T-4 2C-T-7 2C-T-8 2C-T-9 2C-T-13 2C-T-15 2C-T-16 2C-T-17 2C-T-21 2C-TFM 2C-YN Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants: Phenylethanolamine Hordenine Phenethylamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA

Amphetamines	Psychedelics: 3C-BZ 3C-E 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 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 Phenpromethamine 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 MDEA MDHMA MDMA MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others: 3,4-DCA Amiflamine DFMDA Selegiline (also D -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 Pentedrone Pentylone Radafaxine Entactogens: 3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone

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) Theodrenaline Thiamphenicol UWA-101

Chlorphentermine

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Clinical data

Routes of administration	Oral, Insufflated, Rectal
ATC code	A08AA (WHO)
Legal status
Legal status	CA: Schedule IV UK: Class C US: Schedule III
Pharmacokinetic data
Biological half-life	40 hours
Excretion	Renal
Identifiers
IUPAC name 1-(4-chlorophenyl)-2-methylpropan-2-amine
Synonyms	p-Chloro-α,α-dimethylphenethylamine
CAS Number	461-78-9^N 151-06-4
PubChem (CID)	10007
DrugBank	DB01556^Y
ChemSpider	9613^Y
UNII	NHW07912O7^Y
KEGG	C07559^Y
ChEMBL	CHEMBL1201269^N
ECHA InfoCard	100.006.651
Chemical and physical data
Formula	C₁₀H₁₄ClN
Molar mass	183.68 g/mol
3D model (Jmol)	Interactive image
SMILES Clc1ccc(cc1)CC(N)(C)C
InChI InChI=1S/C10H14ClN/c1-10(2,12)7-8-3-5-9(11)6-4-8/h3-6H,7,12H2,1-2H3^Y Key:ZCKAMNXUHHNZLN-UHFFFAOYSA-N^Y
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