Arylcyclohexylamines

Ketamine is a cyclohexanone-derived general anesthetic and NMDA receptor antagonist with analgesic and hallucinogenic properties, used medically for anesthesia, depression, and pain management. Ketamine exists as its two enantiomers, S- (esketamine) and R- (arketamine), and has antidepressant action likely involving other mechanisms in addition to NMDA antagonism.

Methoxetamine (MXE) is a dissociative hallucinogen that has been sold as a designer drug. It differs from many dissociatives such as ketamine and phencyclidine (PCP) that were developed as pharmaceutical drugs for use as general anesthetics in that it was designed specifically to increase the antidepressant effects of ketamine.

Tiletamine is a dissociative anesthetic and pharmacologically classified as an NMDA receptor antagonist. It is an arylcyclohexylamine chemically related to ketamine. Tiletamine hydrochloride exists as odorless white crystals.

4-Phenyl-4-(1-piperidinyl)cyclohexanol, also known as PPC, is an organic chemical which is a metabolite of phencyclidine (PCP). It can be detected in the hair of PCP users.

PCE (Eticyclidine, 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, but research into PCE was not continued after the development of ketamine, a similar drug with more favourable properties. 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.

1-(1-Phenylcyclohexyl)-4-hydroxypiperidine (PCHP) is a metabolite of phencyclidine (PCP). PCHP can be detected in the hair, urine, stool, sweat, and saliva of PCP users.

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.

4-Methoxyphencyclidine (methoxydine, 4-MeO-PCP) is a dissociative anesthetic drug that has been sold online as a research chemical. The synthesis of 4-MeO-PCP was first reported in 1965 by the Parke-Davis medicinal chemist Victor Maddox. A 1999 review published by a chemist using the pseudonym John Q. Beagle suggested the potency of 4-MeO-PCP in man was reduced relative to PCP, two years later Beagle published a detailed description of the synthesis and qualitative effects of 4-MeO-PCP, which he said possessed 70% the potency of PCP. 4-MeO-PCP was the first arylcyclohexylamine research chemica

class=skin-invert-image|thumb|upright|Phencyclidine, the prototypical arylcyclohexylamine derivative. Arylcyclohexylamines, also known as arylcyclohexamines or arylcyclohexanamines, are a chemical class of pharmaceutical, designer, and experimental drugs.

Tenocyclidine (TCP) is a dissociative anesthetic with psychostimulant effects. It was discovered by a team at Parke-Davis in the late 1950s. It is similar in effects to phencyclidine (PCP) but is considerably more potent. TCP has slightly different binding properties to PCP, with more affinity for the NMDA receptors, but less affinity for the sigma receptors. Because of its high affinity for the PCP site of the NMDA receptor complex, the 3H radiolabelled form of TCP is widely used in research into NMDA receptors.

Rolicyclidine (PCPy) is a dissociative anesthetic that is similar in effects to phencyclidine, but is slightly less potent and has fewer stimulant effects. It instead produces a sedative effect described as being somewhat similar to a barbiturate, but with additional PCP-like dissociative, anaesthetic and hallucinogenic 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.

right|thumb|250px|class=skin-invert-image|Metaphit as a methanesulfonate salt

2-Fluorodeschloroketamine (also known as '''2'-Fl-2-Oxo-PCM, fluoroketamine, and 2-FDCK''') is a dissociative anesthetic related to ketamine. Its sale and use as a designer drug has been reported in various countries. It is an analogue of ketamine where the chlorine group has been replaced by fluorine. Due to its recent emergence, the pharmacological specifics of the compound are mostly unclear, but effects are reported to be similar to its parent compound, ketamine.

'''N-Ethylnorketamine (ethketamine, NENK, 2-Cl-2'-Oxo-PCE''') is a designer drug which is presumed to have similar properties to ketamine, a dissociative anesthetic drug with hallucinogenic and sedative effects. It has been sold over the internet since around September 2012, and identified in seized drug samples by analytical laboratories in the UK and other European countries.

Hydroxynorketamine (HNK), or 6-hydroxynorketamine, is a minor metabolite of the anesthetic, dissociative, and antidepressant drug ketamine. It is formed by hydroxylation of the intermediate norketamine, another metabolite of ketamine. As of late 2019, '(2R,6R)-HNK' is in clinical trials for the treatment of depression.

Dieticyclidine (PCDE), or diethylphenylcyclohexylamine, is a psychoactive drug and research chemical of the arylcyclohexylamine chemical class related to phencyclidine (PCP) and eticyclidine (PCE). It acts as an NMDA receptor antagonist but has low potency and acts mainly as a prodrug for eticyclidine.

3-Hydroxyphencyclidine (3-HO-PCP) is a dissociative of the arylcyclohexylamine class related to phencyclidine (PCP) that has been sold online as a designer drug.

PCPr is an arylcyclohexylamine dissociative anesthetic drug with hallucinogenic and stimulant effects. It is around the same potency as phencyclidine, although slightly less potent than the ethyl homologue eticyclidine, and has reportedly been sold as a designer drug in Germany and other European countries since the late 1990s.

Gacyclidine (GK-11, OTO-313) is a psychoactive drug which acts as a dissociative via functioning as a non-competitive NMDA receptor antagonist. It is closely related to phencyclidine (PCP), and specifically, is a derivative of tenocyclidine (TCP). Gacyclidine exhibits neuroprotective effects similar to those of other NMDA receptor antagonists, with the advantage of being substantially less neurotoxic maybe due to its interaction with "non-NMDA" binding sites.

Benocyclidine, also known as benzothiophenylcyclohexylpiperidine (BTCP), is a psychoactive recreational drug of the arylcyclohexylamine class which is related to phencyclidine (PCP). It was first described in a patent application naming Marc Caron and colleagues at Duke University in 1997.

Norketamine, or '''N-desmethylketamine''', is the major active metabolite of ketamine, which is formed mainly by CYP3A4. Similarly to ketamine, norketamine acts as a noncompetitive NMDA receptor antagonist, but is about 3–5 times less potent as an anesthetic in comparison.

Arketamine (developmental code names PCN-101, HR-071603), also known as '(R)-ketamine or (R)-(−)-ketamine', is the (R)-(−) enantiomer of ketamine. Similarly to racemic ketamine and esketamine, the S(+) enantiomer of ketamine, arketamine is biologically active; however, it is less potent as an NMDA receptor antagonist and anesthetic and thus has never been approved or marketed for clinical use as an enantiopure drug. Arketamine is currently in clinical development as a novel antidepressant.