Arylcyclohexylamines

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Phencyclidine (PCP), a well-known arylcyclohexylamine derivative.

Arylcyclohexylamines , also known as arylcyclohexamines or arylcyclohexanamines , are a chemical class of (experimental) medicinal products and designer drugs .

history

Phencyclidine (PCP) is believed to be the first arylcyclohexylamine discovered with recognized anesthetic properties. In the scientific literature, however, several arylcyclohexylamines have been described before PCP, starting with PCA (1-phenylcyclohexan-1-amine), the synthesis of which was first published in 1907. Eticyclidine (PCE) was discovered in 1953 and PCMo in 1954, the latter compound having been described as a potent sedative . Arylcyclohexylamine anesthetics were extensively studied by Parke-Davis , beginning with the synthesis of PCP and later the related compound ketamine in 1956. In the 1970s, these compounds, especially PCP and its analogues , were considered to be due to their dissociative , hallucinogenic and euphoric effects used illegal drugs . Since then, the group of substances has been expanded by scientific research on stimulants , analgesics and neuroprotectants, as well as by chemists looking for novel recreational drugs.

structure

General structure of arylcyclohexylamines

An arylcyclohexylamine consists of a cyclohexylamine which is substituted with an aryl group geminally to the amino group . In the simplest cases, the aryl unit is a phenyl ring , optionally with additional substituents.

The amino group is usually not primary ; the most common N -substituents in the secondary amines are the methyl or ethyl group and the tertiary amines are mostly piperidine and pyrrolidine derivatives .

Pharmacology and pharmacodynamics

Arylcyclohexylamines have different NMDA receptor - antagonistic , dopamine reuptake inhibiting , and μ-opioid receptor - agonistic properties. In addition, they have an agonistic effect on the sigma receptor , antagonistic on nicotine receptors and agonistic on dopamine D 2 receptors . Different pharmacological effects were observed depending on the active ingredients . The antagonism of the NMDA receptor confers anesthetic , antispasmodic , neuroprotective and dissociative effects; the blockade of the dopamine transporter mediates stimulating and euphoric effects as well as psychoses in high doses; and activation of the μ-opioid receptor causes analgesic and euphoric effects. The stimulation of the σ and D2 receptors can also contribute to hallucinogenic and psychotomimetic effects.

Arylcyclohexylamines are versatile active ingredients with a broad spectrum of possible pharmacological effects , depending on the scope and area in which structural chemical modifications have been carried out. The various possibilities of modification of the chemical structure allow a "fine tuning" of the resulting pharmacological and pharmacodynamic profile. z. B. Benocyclidine (BTCP) is a selective dopamine reuptake inhibitor , PCP is primarily an NMDA antagonist, and bromadol (BDPC) is a potent μ-opioid agonist, while PRE-084 is a selective sigma receptor agonist . Thus, radically different pharmacology and pharmacodynamics are possible through different structural combinations.

List of arylcyclohexylamines

structure connection Aryl group Amine group Cyclohexyl ring
1-Phenylcyclohexylamine.svg PCA Phenyl NH 2 -
N-methyl-1-phenylcyclohexylamine.svg PCM Phenyl Methylamine -
N-Ethyl-1-phenylcyclohexylamine.svg Eticyclidine Phenyl Ethylamine -
N-Propyl-1-phenylcyclohexylamine.svg PCPr Phenyl n -propylamine -
N-Isopropyl-1-phenylcyclohexylamine.svg PCiP Phenyl Isopropylamine -
N-Allyl-1-phenylcyclohexylamine.svg PCAL Phenyl Allylamine -
N-Butyl-1-phenylcyclohexylamine.svg PCBu Phenyl n -butylamine -
N- (2-Hydroxyethyl) -1-phenylcyclohexylamine.svg PCEOH Phenyl Hydroxyethylamine -
N- (2-methoxyethyl) -1-phenylcyclohexylamine.svg PCMEA Phenyl Methoxyethylamine -
N- (2-ethoxyethyl) -1-phenylcyclohexylamine.svg PCEEA Phenyl Ethoxyethylamine -
N- (3-methoxypropyl) -1-phenylcyclohexylamine.svg PCMPA Phenyl Methoxypropylamine -
N, N-Dimethyl-1-phenylcyclohexylamine.svg PCDM Phenyl Dimethylamine -
N, N-Diethyl-1-phenylcyclohexylamine.svg Dieticyclidine Phenyl Diethylamine -
2-phenyl-2- (1-piperidinyl) cyclohexanol.svg 2-HO-PCP Phenyl Piperidine 2-hydroxy
1- (2-Methyl-1-phenylcyclohexyl) piperidine.svg 2-Me-PCP Phenyl Piperidine 2-methyl
1- (2-Methoxy-1-phenylcyclohexyl) piperidine.svg 2-MeO-PCP Phenyl Piperidine 2-methoxy
2-phenyl-2- (1-piperidinyl) cyclohexanone.svg 2-keto-PCP Phenyl Piperidine 2-oxo
2-Ethylamino-2-phenylcyclohexanone.svg Eticyclidone ("O-PCE") Phenyl Ethylamine 2-oxo
2-Propylamino-2-phenylcyclohexanone.svg 2-keto-PCPr Phenyl n -propylamine 2-oxo
1- (4-Methyl-1-phenylcyclohexyl) piperidine.svg 4-methyl-PCP Phenyl Piperidine 4-methyl
4-phenyl-4- (1-piperidinyl) cyclohexanone.svg 4-keto-PCP Phenyl Piperidine 4-oxo
1- (1- (2-chlorophenyl) cyclohexyl) piperidine.svg 2'-Cl-PCP o -chlorophenyl Piperidine -
1- (1- (2-methoxyphenyl) cyclohexyl) piperidine.svg 2'-MeO-PCP o -methoxyphenyl Piperidine -
1- (1- (3-fluorophenyl) cyclohexyl) piperidine.svg 3'-F-PCP m -fluorophenyl Piperidine -
1- (1- (3-methylphenyl) cyclohexyl) piperidine.svg 3'-Me-PCP m -Tolyl Piperidine -
1- (1- (3-methylphenyl) cyclohexyl) pyrrolidine.svg 3'-Me-PCPy m -Tolyl Pyrrolidine -
1- (1- (3-aminophenyl) cyclohexyl) piperidine.svg 3'-NH 2 -PCP m -aminophenyl Piperidine -
1- (1- (3-Hydroxyphenyl) cyclohexyl) piperidine.svg 3'-HO-PCP m -hydroxyphenyl Piperidine -
1- (1- (3-methoxyphenyl) cyclohexyl) piperidine.svg 3'-MeO-PCP m -methoxyphenyl Piperidine -
1- (1- (1,3-Benzodioxol-5-yll) cyclohexyl) piperidine.svg 3 ', 4'-MD-PCP 3,4-methylenedioxyphenyl Piperidine -
N-Ethyl-1- (3-methoxyphenyl) cyclohexylamine.svg 3'-MeO-PCE m -methoxyphenyl Ethylamine -
N-Ethyl-1- (3-hydroxyphenyl) cyclohexylamine.svg 3'-HO-PCE m -hydroxyphenyl Ethylamine -
1- (3-Methoxyphenyl) -N-propylcyclohexylamine.svg 3'-MeO-PCPr m -methoxyphenyl n -propylamine -
1- (3-Hydroxyphenyl) -N-propylcyclohexylamine.svg 3'-HO-PCPr m -hydroxyphenyl n -propylamine -
1- (1,3-Benzodioxol-5-yl) -N-propylcyclohexylamine.svg 3 ', 4'-MD-PCPr 3,4-methylenedioxyphenyl n -propylamine -
1- (1- (3-methoxyphenyl) cyclohexyl) pyrrolidine.svg 3'-MeO-PCPy m -methoxyphenyl Pyrrolidine -
1- (1- (4-Hydroxyphenyll) cyclohexyl) piperidine.svg 4'-HO-PCP p -hydroxyphenyl Piperidine -
1- (1- (4-methoxyphenyll) cyclohexyl) piperidine.svg Methoxydine (4'-MeO-PCP) p -methoxyphenyl Piperidine -
N-Ethyl-1- (4-methoxyphenyl) cyclohexylamine.svg 4'-MeO-PCE p -methoxyphenyl Ethylamine -
1- (1- (4-fluorophenyll) cyclohexyl) piperidine.svg 4'-F-PCP p -fluorophenyl Piperidine -
1- (1- (4-fluorophenyll) cyclohexyl) pyrrolidine.svg 4'-F-PCPy p -fluorophenyl Pyrrolidine -
(R) -2- (2-Chlorophenyl) -2-methylaminocyclohexanone.svg Arketamine o -chlorophenyl Methylamine 2-oxo
2-methylamino-2-phenylcyclohexanone.svg Deschloroketamine Phenyl Methylamine 2-oxo
(S) -2- (2-Chlorophenyl) -2-methylaminocyclohexanone.svg Esketamine o -chlorophenyl Methylamine 2-oxo
2- (2-Chlorophenyl) -2-methylaminocyclohexanone.svg Ketamine o -chlorophenyl Methylamine 2-oxo
2-Amino-2- (2-chlorophenyl) -6-hydroxycyclohexanone.svg Hydroxynorketamine o -chlorophenyl NH 2 2-oxo, 6-hydroxy
2- (2-Chlorophenyl) -2-ethylamino-cyclohexanone.svg Ethketamine o -chlorophenyl Ethylamine 2-oxo
2- (2-Chlorophenyl) -2-propylaminocyclohexanone.svg NPNK o -chlorophenyl n -propylamine 2-oxo
2- (2-Methoxyphenyl) -2-methyllaminocyclohexanone.svg Methoxyketamine o -methoxyphenyl Methylamine 2-oxo
2-methylamino-2- (2-methylphenyl) cyclohexanone.svg oMDCK o -Tolyl Methylamine 2-oxo
2-methylamino-2- (3-methylphenyl) cyclohexanone.svg mMDCK m -Tolyl Methylamine 2-oxo
2- (3-Chlorophenyl) -2-methylaminocyclohexanone.svg meta- ketamine m -chlorophenyl Methylamine 2-oxo
4- (2-chlorophenyl) -4-methylaminocyclohexanone.svg iso -ketamines o -chlorophenyl Methylamine 4-oxo
2- (2-Fluorophenyl) -2-methylaminocyclohexanone.svg 2-fluorodeschloroketamine o -fluorophenyl Methylamine 2-oxo
2- (3-Fluorophenyl) -2-methylaminocyclohexanone.svg 3-fluorodeschloroketamine m -fluorophenyl Methylamine 2-oxo
2- (2-bromophenyl) -2-methylaminocyclohexanone.svg Bromoketamine o -Bromophenyl Methylamine 2-oxo
2- (2-Trifluoromethylphenyl) -2-methylaminocyclohexanone.svg TFMDCK o -trifluoromethylphenyl Methylamine 2-oxo
SN35210.svg SN 35210 o -chlorophenyl Carbomethoxybutylamine 2-oxo
2-Ethylamino-2- (3-methoxyphenyl) cyclohexanone.svg Methoxetamine (MXE) m -methoxyphenyl Ethylamine 2-oxo
2- (3-Methoxyphenyl) -2-methylaminocyclohexanone.svg Methoxmetamine m -methoxyphenyl Methylamine 2-oxo
MXPr structure.png MXPr m -methoxyphenyl n -propylamine 2-oxo
HXE structure.png HXE m -hydroxyphenyl Ethylamine 2-oxo
HXM structure.png HXM m -hydroxyphenyl Methylamine 2-oxo
FXE structure.png FXE m -fluorophenyl Ethylamine 2-oxo
Phencyclidine structure.svg Phencyclidine (PCP) Phenyl Piperidine -
PC3MP structure.png PC3MP Phenyl 3-methylpiperidine -
PC4MP structure.png PC4MP Phenyl 4-methylpiperidine -
Rolicyclidine.svg Rolicyclidine (PCPy) Phenyl Pyrrolidine -
PCDMPy structure.png PCDMPy Phenyl 3,3-dimethylpyrrolidine -
PCMo structure.png PCMo Phenyl Morpholine -
2'-MeO-PCMo structure.png Methoxy-PCM (2'-MeO-PCMo) o -methoxyphenyl Morpholine -
3-MeO-PCMo.png 3'-MeO-PCMo m -methoxyphenyl Morpholine -
4'-MeO-PCMo structure.png 4'-MeO-PCMo p -methoxyphenyl Morpholine -
4'-Me-PCMo structure.png Methyl-PCM (4'-Me-PCMo) p -tolyl Morpholine -
2'-Me-4'-HO-PCMo structure.png Hydroxy-methyl-PCM 2-methyl-4-hydroxyphenyl Morpholine -
PYCP structure.png PYCP 2-pyridinyl Piperidine -
TCM structure.png TCM 2-thienyl Methylamine -
TCE structure.png TCE 2-thienyl Ethylamine -
TCPr structure.png TCPr 2-thienyl Propylamine -
Tenocyclidine.svg Tenocyclidine (TCP) 2-thienyl Piperidine -
TCPy structure.png TCPy 2-thienyl Pyrrolidine -
Tiletamine.svg Tiletamine 2-thienyl Ethylamine 2-oxo
Gacyclidine.png Gacyclidine 2-thienyl Piperidine 2-methyl
Bromadol Skeletal.png BDPC p -bromophenyl Dimethylamine 4-phenethyl-4-hydroxy
C-8813.svg C-8813 p -bromophenyl Dimethylamine 4- (thiophen-2-yl) ethyl-4-hydroxy
Dimetamine structure.png Dimetamine p -tolyl Dimethylamine 4-oxo
Ahmadi pcp 2010.svg 3 "-OH-2'-Me-PCP o -Tolyl 3-hydroxypiperidine -
1- (1-PhCHX) -4-Ph-4-OH-piperidine structure.png 4 "- Ph-4" - OH-PCP Phenyl 4-phenyl-4-hydroxypiperidine -
BTCP structure.png BTCP Benzothiophen-2-yl Piperidine -
BTCPy structure.png BTCPy Benzothiophen-2-yl Pyrrolidine -

Analog connections

The structure dependence of the hallucinogenic effects of phencyclidine was investigated by varying the size of the cycloalkane ring. It turns out that the corresponding cyclopentyl compound has about 1/10 of the hallucinogenic activity, while the cycloheptyl and cyclooctyl derivatives are inactive. The homologous compounds are obtained by reacting the respective cycloalkyl ketones with phenylmagnesium bromide . The resulting alcohol is then reacted with sodium azide and then reduced to the amine with lithium aluminum hydride . In the last step the piperidine ring is then built up with 1-5-dibromopentane.

Web links

Individual evidence

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  2. ^ Jason Wallach, Simon D. Brandt: Phencyclidine-Based New Psychoactive Substances . In: Hans H. Maurer, Simon D. Brandt (Eds.): New Psychoactive Substances. Handbook of Experimental Pharmacology . tape 252 . Springer, Cham 2018, ISBN 978-3-03010560-0 , pp. 261-303 .
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