Eticyclidine

Eticyclidine
Clinical data
ATC code	none;
Legal status
Legal status	AU: S9 (Prohibited substance) ; CA: Schedule I ; DE: Anlage I (Authorized scientific use only) ; UK: Class B ; US: Schedule I ;
Identifiers
	show IUPAC name
CAS Number	2201-15-2 ;
PubChem CID	16622;
ChemSpider	15759 ;
UNII	O8I1LL6A89;
ChEMBL	ChEMBL279924 ;
CompTox Dashboard (EPA)	DTXSID2062248 ;
Chemical and physical data
Formula	C14H21N
Molar mass	203.329 g·mol−1
3D model (JSmol)	Interactive image;
	show SMILES
	show InChI

Eticyclidine (PCE, CI-400) is a dissociative anesthetic drug with hallucinogenic effects. It is similar in effects to phencyclidine but is slightly more potent. PCE was developed by Parke-Davis in the 1970s and evaluated for anesthetic potential under the code name CI-400,^[1] but research into PCE was not continued after the development of ketamine, a similar drug with more favourable properties.^[2] PCE is slightly more potent than PCP and has similar effects,^{[medical citation needed]} but its unpleasant taste and tendency to cause nausea made it less accepted by users.^{[citation needed]} Due to its similarity in effects to PCP, PCE was placed into the Schedule 1 list of illegal drugs in the 1970s, although it was only briefly abused in the 1970s and 1980s and is now little known.

References[]

^ Levy L, Cameron DE, Aitken RC (March 1960). "Observation on two psychotomimetic drugs of piperidine derivation--CI 395 (sernyl) and CI 400". The American Journal of Psychiatry. 116 (9): 843–4. doi:10.1176/ajp.116.9.843. PMID 14416411.
^ Kalir A, Edery H, Pelah Z, Balderman D, Porath G (May 1969). "1-Phenycycloalkylamine derivatives. II. Synthesis and pharmacological activity". Journal of Medicinal Chemistry. 12 (3): 473–7. doi:10.1021/jm00303a030. PMID 4977945.

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[pmid14416411-1] Levy L, Cameron DE, Aitken RC (March 1960). "Observation on two psychotomimetic drugs of piperidine derivation--CI 395 (sernyl) and CI 400". The American Journal of Psychiatry. 116 (9): 843–4. doi:10.1176/ajp.116.9.843. PMID 14416411.

[2] Kalir A, Edery H, Pelah Z, Balderman D, Porath G (May 1969). "1-Phenycycloalkylamine derivatives. II. Synthesis and pharmacological activity". Journal of Medicinal Chemistry. 12 (3): 473–7. doi:10.1021/jm00303a030. PMID 4977945.

[1]

[2]

show v t Ionotropic glutamate receptor modulators
AMPAR	Agonists: Main site agonists: 5-Fluorowillardiine AMPA Domoic acid Glutamate Ibotenic acid Proline Quisqualic acid Willardiine; Positive allosteric modulators: Aniracetam BIIB-104 (PF-04958242) Cyclothiazide CX-516 CX-546 CX-614 Farampator (CX-691, ORG-24448) CX-717 CX-1739 Diazoxide Hydrochlorothiazide (HCTZ) IDRA-21 LY-404187 LY-503430 Mibampator (LY-451395) Nooglutyl ORG-26576 Oxiracetam PEPA Piracetam Pramiracetam S-18986 Tulrampator (S-47445, CX-1632) Antagonists: Becampanel Caroverine CNQX Dasolampanel DNQX Fanapanel (MPQX) Kaitocephalin Kynurenic acid Kynurenine Licostinel (ACEA-1021) NBQX Selurampanel Tezampanel Theanine Topiramate Zonampanel; Negative allosteric modulators: Barbiturates (e.g., pentobarbital, sodium thiopental) Cyclopropane Enflurane Ethanol (alcohol) Evans blue GYKI-52466 Halothane Irampanel Isoflurane Perampanel Pregnenolone sulfate Sevoflurane Talampanel; Unknown/unsorted antagonists: Minocycline
KAR	Agonists: Main site agonists: 5-Iodowillardiine AMPA Domoic acid Glutamate Ibotenic acid Kainic acid Proline Quisqualic acid ; Positive allosteric modulators: Cyclothiazide Diazoxide Enflurane Halothane Isoflurane Antagonists: CNQX Dasolampanel DNQX Kaitocephalin Kynurenic acid Licostinel (ACEA-1021) NBQX NS102 Selurampanel Tezampanel Theanine Topiramate UBP-302; Negative allosteric modulators: Barbiturates (e.g., pentobarbital, sodium thiopental) Enflurane Ethanol (alcohol) Evans blue Pregnenolone sulfate
NMDAR	Agonists: Main site agonists: Aspartate Glutamate Homocysteic acid (L-HCA) Homoquinolinic acid Ibotenic acid NMDA Proline Quinolinic acid Tetrazolylglycine Theanine; Glycine site agonists: ACC (ACPC) ACPD Apimostinel (NRX-1074) D-Alanine D-Cycloserine D-Serine Dimethylglycine Glycine HA-966 L-Alanine L-Serine Milacemide Neboglamine (nebostinel) Rapastinel (GLYX-13) Sarcosine; Polyamine site agonists: Neomycin Spermidine Spermine; Other positive allosteric modulators: 24S-Hydroxycholesterol DHEA (prasterone) DHEA sulfate (prasterone sulfate) Pregnenolone sulfate Antagonists: Competitive antagonists: AP5 (APV) AP7 CGP-37849 Kaitocephalin LY-235959 Midafotel (d-CPPene) PEAQX Perzinfotel Selfotel; Glycine site antagonists: 4-Cl-KYN (AV-101) 5,7-DCKA 7-CKA ACC Apimostinel (NRX-1074) AV-101 Carisoprodol CNQX D-Cycloserine DNQX Felbamate Gavestinel Kynurenic acid Kynurenine Licostinel (ACEA-1021) Meprobamate Rapastinel (GLYX-13) ; Polyamine site antagonists: Diaminopropane Diethylenetriamine Huperzine A Putrescine; Uncompetitive pore blockers (mostly dizocilpine site): 2-MDP 3-HO-PCP 3-MeO-PCE 3-MeO-PCMo 3-MeO-PCP 4-MeO-PCP 8A-PDHQ 18-MC α-Endopsychosin Alaproclate Alazocine (SKF-10047) Amantadine Aptiganel Arketamine Budipine Coronaridine Delucemine (NPS-1506) Dexoxadrol Dextrallorphan Dextromethadone Dextromethorphan Dextrorphan Dieticyclidine Diphenidine Dizocilpine Ephenidine Esketamine Etoxadrol Eticyclidine Fluorolintane Gacyclidine Ibogaine Ibogamine Indantadol Ketamine Ketobemidone Lanicemine Levomethadone Levomethorphan Levomilnacipran Levorphanol Loperamide Memantine Methadone Methorphan Methoxetamine Methoxphenidine Milnacipran Morphanol NEFA Neramexane Nitromemantine Noribogaine Norketamine Orphenadrine PCPr PD-137889 Pethidine (meperidine) Phencyclamine Phencyclidine Propoxyphene Remacemide Rhynchophylline Rimantadine Rolicyclidine Sabeluzole Tabernanthine Tenocyclidine Tiletamine Tramadol; Ifenprodil (NR2B) site antagonists: Besonprodil Buphenine (nylidrin) Eliprodil Haloperidol Isoxsuprine Rislenemdaz (CERC-301, MK-0657) Traxoprodil (CP-101606); NR2A-selective antagonists: ; Cations: Hydrogen Magnesium Zinc; Alcohols/volatile anesthetics/related: Benzene Butane Chloroform Cyclopropane Desflurane Diethyl ether Enflurane Ethanol (alcohol) Halothane Hexanol Isoflurane Methoxyflurane Nitrous oxide Octanol Sevoflurane Toluene Trichloroethane Trichloroethanol Trichloroethylene Urethane Xenon Xylene; Unknown/unsorted antagonists: Bumetanide Caroverine Conantokin D-αAA Dexanabinol Flufenamic acid Flupirtine Furosemide Hodgkinsine Metaphit Minocycline MPEP Niflumic acid Pentamidine Pentamidine isethionate Piretanide Psychotridine Transcrocetin (saffron) Unsorted: Allosteric modulators: AGN-241751
See also: Receptor/signaling modulators Metabotropic glutamate receptor modulators Glutamate metabolism/transport modulators

Clinical data

ATC code	none
Legal status
Legal status	AU: S9 (Prohibited substance) CA: Schedule I DE: Anlage I (Authorized scientific use only) UK: Class B US: Schedule I
Identifiers
show IUPAC name N-Ethyl-1-phenylcyclohexylamine
CAS Number	2201-15-2^Y
PubChem CID	16622
ChemSpider	15759^Y
UNII	O8I1LL6A89
ChEMBL	ChEMBL279924^Y
CompTox Dashboard (EPA)	DTXSID2062248
Chemical and physical data
Formula	C₁₄H₂₁N
Molar mass	203.329 g·mol⁻¹
3D model (JSmol)	Interactive image
show SMILES CCNC1(CCCCC1)C2=CC=CC=C2
show InChI InChI=1S/C14H21N/c1-2-15-14(11-7-4-8-12-14)13-9-5-3-6-10-13/h3,5-6,9-10,15H,2,4,7-8,11-12H2,1H3^Y Key:IFYLVUHLOOCYBG-UHFFFAOYSA-N^Y

Eticyclidine

See also[]

References[]