Arylcyclohexylamine
Arylcyclohexylamines, also known as arylcyclohexamines or arylcyclohexanamines, are a
History
Structure
An arylcyclohexylamine is composed of a
Pharmacology
Arylcyclohexylamines varyingly possess
These are versatile agents with a wide range of possible pharmacological activities depending on the extent and range to which chemical modifications are implemented. Thus, radically different pharmacology is possible through different structural combinations.
Notes on numbering
PCP itself is composed of three six-membered rings, which can each be substituted by a variety of groups. These are traditionally numbered in the older research as first the
However, since the widespread sale of these compounds as grey-market designer drugs, nearly all such compounds that have come to prominence either have a bare cyclohexyl ring or a 2-ketocyclohexyl ring, while the piperidine is replaced by a variety of alkyl or cycloalkyl amines and most substitution has taken place on the phenyl ring. Consequently, it is common for widely used phenyl substituted analogues such as
without the prime, even though this is technically incorrect and could lead to confusion.List of arylcyclohexylamines
Structures | Compound | Aryl Substituent | N Group | Cyclohexyl ring | CAS number |
---|---|---|---|---|---|
PCA[24] | Phenyl | NH2 | - | 1934-71-0 | |
PCM[24] | Phenyl | Methylamino | - | 2201-16-3 | |
Eticyclidine | Phenyl | Ethylamino | - | 2201-15-2 | |
PCPr[25] | Phenyl | n-Propylamino | - | 18949-81-0 | |
PCiP | Phenyl | Isopropylamino | - | 1195-42-2 | |
PCAL [26] | Phenyl | Allylamino | - | 2185-95-7 | |
PCBu | Phenyl | n-Butylamino | - | 73166-29-7 | |
PCEOH | Phenyl | Hydroxyethylamino | - | 2201-22-1 | |
PCMEA[27] | Phenyl | Methoxyethylamino | - | 2201-57-2 | |
PCEEA | Phenyl | Ethoxyethylamino | - | 1072895-05-6 | |
PCMPA | Phenyl | Methoxypropylamino | - | 2201-58-3 | |
PCDM[24] | Phenyl | Dimethylamino | - | 2201-17-4 | |
Dieticyclidine | Phenyl | Diethylamino | - | 2201-19-6 | |
2-HO-PCP[6] | Phenyl | Piperidine | 2-Hydroxy | 94852-58-1 | |
2-Me-PCP[28] | Phenyl | Piperidine | 2-Methyl | 59397-29-4 | |
2-MeO-PCP[29] | Phenyl | Piperidine | 2-Methoxy | 78636-34-7 | |
2-Keto-PCP | Phenyl | Piperidine | 2-Keto | 101688-16-8 | |
Eticyclidone ("O-PCE") |
Phenyl | Ethylamino | 2-Keto | 6740-82-5 | |
2-Keto-PCPr | Phenyl | n-Propylamino | 2-Keto | ||
4-Methyl-PCP | Phenyl | Piperidine | 4-Methyl | 19420-52-1 | |
4-Keto-PCP[30] | Phenyl | Piperidine | 4-Keto | 65620-13-5 | |
2'-Cl-PCP | o-Chlorophenyl | Piperidine | - | 2201-31-2 | |
3'-Cl-PCP | m-Chlorophenyl | Piperidine | - | 2201-32-3 | |
2'-MeO-PCP | o-Methoxyphenyl | Piperidine | - | 2201-34-5 | |
3'-F-PCP[31] | m-Fluorophenyl | Piperidine | - | 89156-99-0 | |
3'-Me-PCP[32] | m-Tolyl | Piperidine | - | 2201-30-1 | |
3'-Me-PCPy | m-Tolyl | Pyrrolidine | - | 1622348-63-3 | |
3'-NH2-PCP | m-Aminophenyl | Piperidine | - | 72242-00-3 | |
3'-HO-PCP | m-Hydroxyphenyl | Piperidine | - | 79787-43-2 | |
3'-MeO-PCP | m-Methoxyphenyl | Piperidine | - | 72242-03-6 | |
3',4'-MD-PCP | 3,4-Methylenedioxyphenyl | Piperidine | - | ||
3'-MeO-PCE | m-Methoxyphenyl | Ethylamino | - | 1364933-80-1 | |
3'-HO-PCE | m-Hydroxyphenyl | Ethylamino | - | ||
3'-MeO-PCPr | m-Methoxyphenyl | n-Propylamino | - | 1364933-81-2 | |
3'-HO-PCPr | m-Hydroxyphenyl | n-Propylamino | - | ||
3',4'-MD-PCPr | 3,4-Methylenedioxyphenyl | n-Propylamino | - | ||
3'-MeO-PCPy[32] | m-Methoxyphenyl | Pyrrolidine | - | 1364933-79-8 | |
4'-HO-PCP | p-Hydroxyphenyl | Piperidine | - | 66568-88-5 | |
Methoxydine (4'-MeO-PCP) |
p-Methoxyphenyl | Piperidine | - | 2201-35-6 | |
4'-MeO-PCE | p-Methoxyphenyl | Ethylamino | - | ||
4'-F-PCP[31] | p-Fluorophenyl | Piperidine | - | 22904-99-0 | |
4'-F-PCPy | p-Fluorophenyl | Pyrrolidine | - | ||
Arketamine | o-Chlorophenyl | Methylamino | 2-Keto | 33643-49-1 | |
Deschloroketamine | Phenyl | Methylamino | 2-Keto | 7063-30-1 | |
Esketamine | o-Chlorophenyl | Methylamino | 2-Keto | 33643-46-8 | |
Ketamine | o-Chlorophenyl | Methylamino | 2-Keto | 6740-88-1 | |
Hydroxynorketamine | o-Chlorophenyl | NH2 | 2-Keto, 6-Hydroxy | 81395-70-2 | |
Ethketamine | o-Chlorophenyl | Ethylamino | 2-Keto | 1354634-10-8 | |
NPNK | o-Chlorophenyl | n-Propylamino | 2-Keto | 2749326-65-4 | |
Methoxyketamine | o-Methoxyphenyl | Methylamino | 2-Keto | 7063-51-6 | |
2-MeO-NEK[33] | o-Methoxyphenyl | Ethylamino | 2-Keto | ||
oMDCK[34] | o-Tolyl | Methylamino | 2-Keto | 7063-37-8 | |
mMDCK | m-Tolyl | Methylamino | 2-Keto | ||
meta-Ketamine | m-Chlorophenyl | Methylamino | 2-Keto | 7063-53-8 | |
iso-Ketamine | o-Chlorophenyl | Methylamino | 4-Keto | ||
2-Fluorodeschloroketamine | o-Fluorophenyl | Methylamino | 2-Keto | 111982-50-4 | |
3-Fluorodeschloroketamine | m-Fluorophenyl | Methylamino | 2-Keto | 2657761-23-2 | |
Bromoketamine |
o-Bromophenyl | Methylamino | 2-Keto | 120807-70-7 | |
TFMDCK | o-Trifluoromethylphenyl | Methylamino | 2-Keto | 1782149-73-8 | |
SN 35210[35] | o-Chlorophenyl | Carbomethoxybutylamino | 2-Keto | 1450615-41-4 | |
Methoxetamine | m-Methoxyphenyl | Ethylamino | 2-Keto | 1239943-76-0 | |
Methoxmetamine | m-Methoxyphenyl | Methylamino | 2-Keto | 1781829-56-8 | |
Methoxpropamine | m-Methoxyphenyl | n-Propylamino | 2-Keto | 2504100-71-2 | |
MXiPr |
m-Methoxyphenyl | i-Propylamino | 2-Keto | ||
Ethoxetamine | m-Ethoxyphenyl | Ethylamino | 2-Keto | ||
Deoxymethoxetamine (3-Me-2'-Oxo-PCE) | m-Tolyl | Ethylamino | 2-Keto | 2666932-45-0 | |
Br-MXE | 2-bromo-5-methoxyphenyl | Ethylamino | 2-Keto | ||
Hydroxetamine (HXE) | m-Hydroxyphenyl | Ethylamino | 2-Keto | 1620054-73-0 | |
HXM | m-Hydroxyphenyl | Methylamino | 2-Keto | ||
2F-NENDCK | o-Fluorophenyl | Ethylamino | 2-Keto | ||
Fluorexetamine (FXE) | m-Fluorophenyl | Ethylamino | 2-Keto | ||
Phencyclidine (PCP) | Phenyl | Piperidine | - | 77-10-1 | |
PC3MP | Phenyl | 3-Methylpiperidine | - | 2201-41-4 | |
PC4MP | Phenyl | 4-Methylpiperidine | - | 2201-42-5 | |
Rolicyclidine (PCPy) | Phenyl | Pyrrolidine | - | 2201-39-0 | |
PCDMPy | Phenyl | 3,3-Dimethylpyrrolidine | - | ||
PCMo | Phenyl | Morpholine | - | 2201-40-3 | |
Methoxy-PCM[7] (2'-MeO-PCMo) | o-Methoxyphenyl | Morpholine | - | 1314323-88-0 | |
3'-MeO-PCMo | m-Methoxyphenyl | Morpholine | - | 138873-80-0 | |
4'-MeO-PCMo | p-Methoxyphenyl | Morpholine | - | ||
Methyl-PCM[36] (4'-Me-PCMo) | p-Tolyl | Morpholine | - | 120803-52-3 | |
Hydroxy-methyl-PCM | 2-Methyl-4-hydroxyphenyl | Morpholine | - | 1314323-89-1 | |
PYCP [37] | 2-Pyridinyl | Piperidine | - | ||
TCM | 2-Thienyl | Methylamino | - | 139401-07-3 | |
TCE | 2-Thienyl | Ethylamino | - | 101589-62-2 | |
TCPr [38] | 2-Thienyl | Propylamino | - | ||
Tenocyclidine (TCP) | 2-Thienyl | Piperidine | - | 21500-98-1 | |
T3CP | 3-Thienyl | Piperidine | - | 19420-50-9 | |
TCPy | 2-Thienyl | Pyrrolidine | - | 22912-13-6 | |
Tiletamine | 2-Thienyl | Ethylamino | 2-Keto | 14176-49-9 | |
MXTE | 4-Methoxy-2-thienyl | Ethylamino | 2-Keto | ||
Gacyclidine | 2-Thienyl | Piperidine | 2-Methyl | 68134-81-6 | |
BDPC |
p-Bromophenyl | Dimethylamino | 4-Phenethyl-4-hydroxy | 77239-98-6 | |
C-8813 | p-Bromophenyl | Dimethylamino | 4-(thiophen-2-yl)ethyl-4-hydroxy | 616898-54-5 | |
Dimetamine[39] | p-Tolyl | Dimethylamino | 4-Keto | 65619-06-9 | |
3''-OH-2'-Me-PCP [40] | o-Tolyl | 3-Hydroxypiperidine | - | ||
4''-Ph-4''-OH-PCP [41] | Phenyl | 4-Phenyl-4-hydroxypiperidine | - | 77179-39-6 | |
BTCP[42] | Benzothiophen-2-yl | Piperidine | - | 112726-66-6 | |
BTCPy[10] | Benzothiophen-2-yl | Pyrrolidine | - | ||
GK-189[43] | Naphthalen-2-yl | Piperidine | - | 81490-58-6 |
Related compounds
Other similar compounds exist where the base ring has been varied, or the amine chain replaced with other groups.[44] More cycloalkane ring sizes have been experimented with than just purely thinking in terms of the cyclohexylamine. The cyclopentyl homologue of PCP is active with around one-tenth the potency,[45] while the cycloheptyl and cyclooctyl derivatives are inactive, though some substituted arylcycloheptylamines retain activity.[46] The requisite cycloalkylketone is reacted with PhMgBr; 3° alcohol is then reacted with NaN3; azide then reduced with LAH. Then in the final step the piperidine ring is constructed with 1-5-dibromo-pentane.[47] Other compounds are known where the cyclohexyl base ring is replaced by rings such as norbornyl, adamantyl,[48] tetralin, oxane, thiane [49] or piperidine.[50] Conformationally constrained analogs have been prepared and researched by Morieti et al.[51]
Structure | Compound | Aryl Substituent | N Group | Base ring | CAS number |
---|---|---|---|---|---|
PCPEP | Phenyl | Piperidine | Cyclopentyl | 23036-19-3 | |
3F-PCHEPy | 3-Fluorophenyl | Pyrrolidine | Cycloheptyl | ||
3-MeO-PBCHP | 3-Methoxyphenyl | Piperidine | Bicyclo[2.2.1]heptane | ||
PADP (P2AP) | Phenyl | Piperidine | Adamantyl | 72241-99-7 | |
3-MeO-PTP | 3-Methoxyphenyl | Piperidine | Tetralin | ||
HHFA | Fused phenyl | Amino | Hexahydrofluorene | ||
DHPQ | Phenyl | Decahydroquinoline | |||
POXP | Phenyl | Piperidine | Oxane | ||
PTHP | Phenyl | Piperidine | Thiane | ||
MPBPip | Phenyl | Piperidine | N-Methylpiperidine | 36882-04-9 | |
BnCP | Benzyl | Piperidine | Cyclohexyl | 22912-07-8 | |
YNCP | Ethynyl | Piperidine | Cyclohexyl | 51165-02-7 | |
ALCP | Allyl | Piperidine | Cyclohexyl | 7418-80-6 | |
Piritramide | Replaced by carboxamide | Piperidine | N-(3-cyano-3,3-diphenylpropyl)piperidine | 302-41-0 | |
PRE-084 | Phenyl | Morpholinylethylcarboxylate | Cyclohexyl | 138847-85-5 | |
Clofenciclan | p-Chlorophenyl | Diethylaminoethoxy | Cyclohexyl | 5632-52-0 |
References
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Further reading
- Morris H, Wallach J (2014). "From PCP to MXE: a comprehensive review of the non-medical use of dissociative drugs". Drug Testing and Analysis. 6 (7–8): 614–32. PMID 24678061.