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3-methoxyphencyclidine

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3-methoxyphencyclidine

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3-Methoxyphencyclidine (3-MeO-PCP) is a dissociative hallucinogen of the arylcyclohexylamine class related to phencyclidine (PCP) which has been sold online as a designer drug. It has been used across Europe and the United States. In some cases, consumption has been known to be fatal. It acts mainly as an NMDA receptor antagonist, though it has also been found to interact with the sigma σ receptor and the serotonin transporter. The drug does not possess any opioid activity nor does it act as a dopamine reuptake inhibitor.

Chemical data

Formula
C18H27NO
Molecular weight
273.4 g/mol
IUPAC name
1-[1-(3-methoxyphenyl)cyclohexyl]piperidine
SMILES
COC1=CC=CC(=C1)C2(CCCCC2)N3CCCCC3
InChIKey
BQQSZHHKGPOXLN-UHFFFAOYSA-N
XLogP
3.6
Polar surface area
12.5 Ų
H-bond donors
0
H-bond acceptors
2
Formal charge
0

via PubChem

Wikidata facts

Mass
273.209
Show 3 more facts
chemical formula
C₁₈H₂₇NO
canonical SMILES
COC1=CC=CC(=C1)C2(CCCCC2)N3CCCCC3
Commons category
3-Methoxyphencyclidine
Sources (2)

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Encyclopedic overview

16 sections
Contents
  • Pharmacology
  • Chemistry
  • History
  • Society and culture
  • Recreational use
  • Legal status
  • United Kingdom
  • United States
  • Canada
  • Sweden
  • Czech Republic
  • Chile
  • Portugal
  • See also
  • References
  • External links

3-Methoxyphencyclidine (3-MeO-PCP) is a dissociative hallucinogen of the arylcyclohexylamine class related to phencyclidine (PCP) which has been sold online as a designer drug. It has been used across Europe and the United States. In some cases, consumption has been known to be fatal. It acts mainly as an NMDA receptor antagonist, though it has also been found to interact with the sigma σ receptor and the serotonin transporter. The drug does not possess any opioid activity nor does it act as a dopamine reuptake inhibitor.

==Pharmacology== 3-MeO-PCP has a K of 20 nM for the dizocilpine (MK-801) site of the NMDA receptor, 216 nM for the serotonin transporter (SERT), and 42 nM for the sigma σ receptor. It does not bind to the norepinephrine or dopamine transporter nor to the sigma σ receptor (Ki >10,000 nM). Based on its structural similarity to 3-hydroxy-PCP (3-HO-PCP), which uniquely among arylcyclohexylamines has high affinity for the μ-opioid receptor in addition to the NMDA receptor, it was initially expected that 3-MeO-PCP would have opioid activity. However, radioligand binding assays with human proteins have shown that, contrary to common belief, the drug also does not interact with the μ-, δ-, or κ-opioid receptors at concentrations of up to 10,000 nM. As such, the notion that 3-MeO-PCP has opioid activity has been described as a myth.

Excerpted from Wikipedia’s “3-methoxyphencyclidine” article, available under the CC BY-SA 4.0 licence.

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