Cericlamine

Cericlamine
Clinical data
Routes of; administration	Oral
ATC code	None;
Pharmacokinetic data
Elimination half-life	8 hours
Identifiers
	IUPAC name 3-(3,4-Dichlorophenyl)-2-(dimethylamino)-2-methylpropan-1-ol;
CAS Number	112922-55-1;
PubChem CID	131074;
ChemSpider	115890;
UNII	VES82D23IB;
CompTox Dashboard (EPA)	DTXSID00869558 ;
Chemical and physical data
Formula	C12H17Cl2NO
Molar mass	262.17 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(CC1=CC(=C(C=C1)Cl)Cl)(CO)N(C)C;
	InChI InChI=1S/C12H17Cl2NO/c1-12(8-16,15(2)3)7-9-4-5-10(13)11(14)6-9/h4-6,16H,7-8H2,1-3H3; Key:FWYRGHMKHZXXQX-UHFFFAOYSA-N;

Cericlamine (INN; developmental code JO-1017) is a potent and moderately selective serotonin reuptake inhibitor (SSRI) of the amphetamine family (specifically, a derivative of phentermine, and closely related to chlorphentermine, a highly selective serotonin releasing agent) that was investigated as an antidepressant for the treatment of depression, anxiety disorders, and anorexia nervosa by Jouveinal but did not complete development and was never marketed.^[1]^[2]^[3]^[4] It reached phase III clinical trials in 1996 before development was discontinued in 1999.^[5]

Synthesis

Arylation of methacrylic acid with a diazonium salt of 3,4-dichloroaniline (or 3,4-dichloro-benzenediazonium salt), is carried out according to the Meerwein reaction catalysed by a metallic halide. For the next step, the halide is displaced by dimethylamine, then esterification is performed, followed by reduction with a metal hydride.

References

^ ^a ^b ^c Darcourt G, Tessera M, Lesaunier R, Engrand P, Scherrer B, Dreyfus J, Bogaievsky Y (1992). "A Multicentre Double-Blind, Placebo-Controlled Dose-Finding Study with Cericlamine in Major Depression". Clinical Neuropharmacology. 15: 176B. doi:10.1097/00002826-199202001-00339. ISSN 0362-5664.
^ Crow S, Brown E (March 2003). "Investigational drugs for eating disorders". Expert Opinion on Investigational Drugs. 12 (3): 491–9. doi:10.1517/13543784.12.3.491. PMID 12605570.
^ Ramesh N. Patel (3 January 2000). Stereoselective Biocatalysis. CRC Press. pp. 48–. ISBN 978-0-8247-8282-5.
^ Tang LC, Tang SJ (6 December 2012). Neurochemistry in Clinical Application. Springer Science & Business Media. pp. 81–. ISBN 978-1-4615-1857-0.
^ "Cericlamine". AdisInsight. Springer Nature Switzerland AG. Retrieved 13 January 2016.
^ US 6121491, Nicolas M, Laboue B, Depernet D, "Process for the preparation of (+/-)3-(3,4-dichlorophenyl)-2-dimethylamino-2-methylpropan-1-OL or cericlamine", issued 19 September 200, assigned to Warner Lambert

[DarcourtTessera1992-1] Darcourt G, Tessera M, Lesaunier R, Engrand P, Scherrer B, Dreyfus J, Bogaievsky Y (1992). "A Multicentre Double-Blind, Placebo-Controlled Dose-Finding Study with Cericlamine in Major Depression". Clinical Neuropharmacology. 15: 176B. doi:10.1097/00002826-199202001-00339. ISSN 0362-5664.

[CrowBrown2003-2] Crow S, Brown E (March 2003). "Investigational drugs for eating disorders". Expert Opinion on Investigational Drugs. 12 (3): 491–9. doi:10.1517/13543784.12.3.491. PMID 12605570.

[Patel2000-3] Ramesh N. Patel (3 January 2000). Stereoselective Biocatalysis. CRC Press. pp. 48–. ISBN 978-0-8247-8282-5.

[TangTang2012-4] Tang LC, Tang SJ (6 December 2012). Neurochemistry in Clinical Application. Springer Science & Business Media. pp. 81–. ISBN 978-1-4615-1857-0.

[AdisInsight-5] "Cericlamine". AdisInsight. Springer Nature Switzerland AG. Retrieved 13 January 2016.

[6] US 6121491, Nicolas M, Laboue B, Depernet D, "Process for the preparation of (+/-)3-(3,4-dichlorophenyl)-2-dimethylamino-2-methylpropan-1-OL or cericlamine", issued 19 September 200, assigned to Warner Lambert

[1]

[2]

[3]

[4]

[5]

[6]

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-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-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: BOH 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 (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 N-Ethylhexedrone N-Ethylpentedrone 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) Solriamfetol Theodrenaline Thiamphenicol UWA-101 Venlafaxine

Synthesis

See also

References