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Rolicyclidine

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Identification

Generic Name
Rolicyclidine
DrugBank Accession Number
DB01549
Background

Rolicyclidine (PCPy) is classified as a dissociative anesthetic agent. It also has hallucinogenic and sedative properties. Because of its pharmacodynamic similarity to the drug phencyclidine (PCP), rolicyclidine was added to the Schedule I list of illegal drugs in the USA in the 1970s.

Type
Small Molecule
Groups
Experimental, Illicit
Structure
3D
Similar Structures
Weight
Average: 229.3605
Monoisotopic: 229.183049741
Chemical Formula
C16H23N
Synonyms
  • 1-(1-phenylcyclohexyl)pyrrolidine
  • PCPy
  • Roliciclidina
  • Rolicyclidine
  • Rolicyclidinum
External IDs
  • DEA No. 7458
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Pharmacology

Indication

Rolicyclidine has anesthetic properties and can induce a sedative effect.

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Contraindications & Blackbox Warnings
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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.

TargetActionsOrganism
AGlutamate receptor ionotropic, NMDA 3ANot AvailableHumans
AD(2) dopamine receptor
inhibitor
Humans
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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
Kingdom
Organic compounds
Super Class
Organic nitrogen compounds
Class
Organonitrogen compounds
Sub Class
Amines
Direct Parent
Aralkylamines
Alternative Parents
Cyclohexylamines / N-alkylpyrrolidines / Benzene and substituted derivatives / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Aralkylamine / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Cyclohexylamine / Hydrocarbon derivative / Monocyclic benzene moiety / N-alkylpyrrolidine / Organoheterocyclic compound / Organopnictogen compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
tertiary amine, pyrrolidines (CHEBI:60805)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
183O9O9JE3
CAS number
2201-39-0
InChI Key
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
IUPAC Name
1-(1-phenylcyclohexyl)pyrrolidine
SMILES
C1CCN(C1)C1(CCCCC1)C1=CC=CC=C1

References

General References
Not Available
PubChem Compound
62436
PubChem Substance
46507433
ChemSpider
56218
ChEBI
60805
ChEMBL
CHEMBL1719398
ZINC
ZINC000001481918
Wikipedia
Rolicyclidine

Clinical Trials

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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
PropertyValueSource
Water Solubility0.0239 mg/mLALOGPS
logP4.54ALOGPS
logP4.04Chemaxon
logS-4ALOGPS
pKa (Strongest Basic)10.7Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count1Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area3.24 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity73.05 m3·mol-1Chemaxon
Polarizability27.69 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9972
Blood Brain Barrier+0.9934
Caco-2 permeable+0.8046
P-glycoprotein substrateSubstrate0.5
P-glycoprotein inhibitor INon-inhibitor0.7688
P-glycoprotein inhibitor IINon-inhibitor0.5156
Renal organic cation transporterInhibitor0.7688
CYP450 2C9 substrateNon-substrate0.7933
CYP450 2D6 substrateNon-substrate0.8981
CYP450 3A4 substrateNon-substrate0.5381
CYP450 1A2 substrateInhibitor0.5635
CYP450 2C9 inhibitorNon-inhibitor0.9091
CYP450 2D6 inhibitorInhibitor0.9172
CYP450 2C19 inhibitorNon-inhibitor0.5905
CYP450 3A4 inhibitorNon-inhibitor0.8459
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8619
Ames testNon AMES toxic0.8221
CarcinogenicityNon-carcinogens0.9
BiodegradationNot ready biodegradable0.9638
Rat acute toxicity3.3265 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8025
hERG inhibition (predictor II)Inhibitor0.6536
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0190000000-70dfe08829f59b35ae4a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ac0-8940000000-8a97f951f9d4005bd038
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0090000000-0b89b5b526ab6cdfc3ac
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-06ur-9810000000-9321300b2f593c83c4a3
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0090000000-232a4e7a5fe6f803ef66
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-053r-9510000000-f9229741228342b51331
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-157.7772189
predicted
DarkChem Lite v0.1.0
[M-H]-156.53249
predicted
DeepCCS 1.0 (2019)
[M+H]+158.6524189
predicted
DarkChem Lite v0.1.0
[M+H]+158.89049
predicted
DeepCCS 1.0 (2019)
[M+Na]+164.98363
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Glutamate receptor ionotropic, NMDA 3A
Kind
Protein
Organism
Humans
Pharmacological action
Yes
General Function
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. During the development of neural circuits, plays a role in the synaptic refinement period, restricting spine maturation and growth. By competing with GIT1 interaction with ARHGEF7/beta-PIX, may reduce GIT1/ARHGEF7-regulated local activation of RAC1, hence affecting signaling and limiting the maturation and growth of inactive synapses. May also play a role in PPP2CB-NMDAR mediated signaling mechanism
Specific Function
calcium channel activity
Gene Name
GRIN3A
Uniprot ID
Q8TCU5
Uniprot Name
Glutamate receptor ionotropic, NMDA 3A
Molecular Weight
125464.07 Da
References
  1. Leung K: 4-Acetoxy-7-chloro-3-(3-(-4-[11C]methoxybenzyl)phenyl)-2(1H)-quinolone . [Article]
  2. 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. doi: 10.1371/journal.pone.0011374. [Article]
Details2. D(2) dopamine receptor
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase (PubMed:21645528). Positively regulates postnatal regression of retinal hyaloid vessels via suppression of VEGFR2/KDR activity, downstream of OPN5 (By similarity)
Specific Function
dopamine binding
Gene Name
DRD2
Uniprot ID
P14416
Uniprot Name
D(2) dopamine receptor
Molecular Weight
50618.91 Da
References
  1. 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. doi: 10.1002/syn.20647. [Article]
  2. Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Drug created at July 31, 2007 13:10 / Updated at August 26, 2024 19:22