DrugBank: Rolicyclidine (DB01549)

targets (2)

Identification

Name

Rolicyclidine

Accession Number

DB01549

Type

small molecule

Groups

illicit, experimental

Description

Rolicyclidine (PCPy) is a dissociative anesthetic drug with hallucinogenic and sedative effects. Due to its similarity in effects to PCP, PCPy was placed into the Schedule I list of illegal drugs in the 1970s, although it has never been widely abused and is now little known.

Structure

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

1-(1-phenylcyclohexyl)pyrrolidine
DEA No. 7458
PCPy
Pyrrolidine analog of phencyclidine
Roliciclidina [INN-Spanish]
Rolicyclidinum [INN-Latin]

Salts

Not Available

Brand names

Not Available

Brand mixtures

Not Available

Categories

Hallucinogens

CAS number

2201-39-0

Weight

Average: 229.3605
Monoisotopic: 229.183049741

Chemical Formula

C₁₆H₂₃N

InChI Key

InChIKey=FYOWWXMGDATDQY-UHFFFAOYSA-N

InChI

InChI=1S/C16H23N/c1-3-9-15(10-4-1)16(11-5-2-6-12-16)17-13-7-8-14-17/h1,3-4,9-10H,2,5-8,11-14H2

Plain Text

IUPAC Name

1-(1-phenylcyclohexyl)pyrrolidine

SMILES

C1CCN(C1)C1(CCCCC1)C1=CC=CC=C1

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Not Available

Classes

Not Available

Substructures

Not Available

Pharmacology

Indication

Rolicyclidine has anesthetic properties and can induce a sedative effect.

Pharmacodynamics

Rolicyclidine is similar in effects to phencyclidine but is slightly less potent and has less stimulant effects. Instead it acts by inducing a sedative effect described as being somewhat similar to a barbiturate, but with additional PCP-like dissociative, anaesthetic and hallucinogenic effects.

Mechanism of action

Rolicyclidine works primarily as an NMDA receptor antagonist, which blocks the activity of the NMDA Receptor.

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

Not Available

Half life

Not Available

Clearance

Not Available

Toxicity

Not Available

Affected organisms

Humans and other mammals

Pathways

Not Available

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage forms

Not Available

Prices

Not Available

Patents

Not Available

Properties

State

solid

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
water solubility	2.39e-02 g/l	ALOGPS
logP	4.54	ALOGPS
logP	4.04	ChemAxon
logS	-4	ALOGPS
pKa (strongest basic)	10.78	ChemAxon
physiological charge	1	ChemAxon
hydrogen acceptor count	1	ChemAxon
hydrogen donor count	0	ChemAxon
polar surface area	3.24	ChemAxon
rotatable bond count	2	ChemAxon
refractivity	73.05	ChemAxon
polarizability	27.69	ChemAxon

References

Synthesis Reference

Not Available

General Reference

Not Available

External Links

Resource	Link
PubChem Compound	62436
PubChem Substance	46507433
ChemSpider	56218
ChEBI	60805
ChEMBL	60805
Wikipedia	http://en.wikipedia.org/wiki/Rolicyclidine

ATC Codes

Not Available

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

Not Available

Interactions

Drug Interactions

Not Available

Food Interactions

Not Available

Targets
1. Glutamate [NMDA] receptor subunit 3A Pharmacological action: yes NMDA receptor subtype of glutamate-gated ion channels with reduced single-channel conductance, low calcium permeability and low voltage-dependent sensitivity to magnesium. Mediated by glycine. May play a role in the development of dendritic spines. May play a role in PPP2CB-NMDAR mediated signaling mechanism Organism class: human UniProt ID: Q8TCU5 Gene: GRIN3A Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Leung K: 4-Acetoxy-7-chloro-3-(3-(-4-[11C]methoxybenzyl)phenyl)-2(1H)-quinolone Pubmed Yuede CM, Wozniak DF, Creeley CE, Taylor GT, Olney JW, Farber NB: Behavioral consequences of NMDA antagonist-induced neuroapoptosis in the infant mouse brain. PLoS One. 2010 Jun 29;5(6):e11374. Pubmed 2. D(2) dopamine receptor Pharmacological action: unknown This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase Organism class: human UniProt ID: P14416 Gene: DRD2 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Seeman P, Guan HC, Hirbec H: Dopamine D2High receptors stimulated by phencyclidines, lysergic acid diethylamide, salvinorin A, and modafinil. Synapse. 2009 Aug;63(8):698-704. Pubmed

Targets

1. Glutamate [NMDA] receptor subunit 3A

Pharmacological action: yes

NMDA receptor subtype of glutamate-gated ion channels with reduced single-channel conductance, low calcium permeability and low voltage-dependent sensitivity to magnesium. Mediated by glycine. May play a role in the development of dendritic spines. May play a role in PPP2CB-NMDAR mediated signaling mechanism

Organism class: human
UniProt ID: Q8TCU5 Link_out

Gene: GRIN3A Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Leung K: 4-Acetoxy-7-chloro-3-(3-(-4-[11C]methoxybenzyl)phenyl)-2(1H)-quinolone Pubmed
Yuede CM, Wozniak DF, Creeley CE, Taylor GT, Olney JW, Farber NB: Behavioral consequences of NMDA antagonist-induced neuroapoptosis in the infant mouse brain. PLoS One. 2010 Jun 29;5(6):e11374. Pubmed

2. D(2) dopamine receptor

Pharmacological action: unknown

This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase

Organism class: human
UniProt ID: P14416 Link_out

Gene: DRD2 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Seeman P, Guan HC, Hirbec H: Dopamine D2High receptors stimulated by phencyclidines, lysergic acid diethylamide, salvinorin A, and modafinil. Synapse. 2009 Aug;63(8):698-704. Pubmed

Comments

Drug created on July 31, 2007 07:10 / Updated on February 08, 2013 16:20