EXP-561

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EXP-561
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Clinical data
Routes of
administration		Oral
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  • none
Legal status
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  • In general: uncontrolled
Identifiers
  • 4-phenylbicyclo[2.2.2]octan-1-amine
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Chemical and physical data
FormulaC14H19N
Molar mass201.313 g·mol−1
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  • NC12CCC(CC1)(CC2)C3=CC=CC=C3
  • InChI=1S/C14H19N.ClH/c15-14-9-6-13(7-10-14,8-11-14)12-4-2-1-3-5-12;/h1-5H,6-11,15H2;1H
  • Key:LTHJBDQSFIGMAZ-UHFFFAOYSA-N
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EXP-561[1] is an investigational drug that acts as an inhibitor of the reuptake of serotonin, dopamine, and norepinephrine.[2][3][4][5] It was developed in the 1960s by Du Pont[6] and was suggested as a potential antidepressant but failed in trials[7] and was never marketed.[5][8][9][10]

SAR simplification in the molecular structure leads to a compound called 4-Phenylcyclohexylamine [19992-45-1].[11] This is produced by reduction of the oxime of a commercially available compound that is called 4-phenylcyclohexanone. It is noteworthy to point out that this precursor might forseeably share a dual use in the synthesis of danavorexton.

In one method of synthesis, EXP-561 is made from a chemical that is called 3-carboethoxy-6-phenyl-2-pyrone [6465-14-1]. The disadvantage of this method is that it needed to be heated with ethylene in benzene solvent at 200C for 16 hours at 1000 atmospheres, so a suitable pressure vessel was needed. Although, alternative protocols were addressed that sought to circumvent this limitation.[12] However, this much pressure seemed excessive and a more recent patent only employed 75 bar pressure.

See also

References

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  1. ^ Page Template:Citation/styles.css has no content.US 3362878, Snyder JA, "Pharmaceutical compositions and methods utilizing substituted bicyclo[2.2.2]-octanes", issued Script error: No such module "auto date formatter"., assigned to EIDP Inc. 
  2. ^ Page Module:Citation/CS1/styles.css has no content.Fuller RW, Snoddy HD, Perry KW (November 1976). "Inhibition of amine uptake by 4-phenyl-bicyclo(2,2,2)octan-1-amine hydrochloride monohydrate (EXP 561) in rats". biochemical Pharmacology. 25 (21): 2409–2410. doi:10.1016/0006-2952(76)90039-3. PMID 999731.
  3. ^ Page Module:Citation/CS1/styles.css has no content.BK K (December 1976). "Molecular geometry of inhibitors of the uptake of catecholamines and serotonin in synaptosomal preparations of rat brain". The Journal of Pharmacology and Experimental Therapeutics. 199 (3): 649–661. doi:10.1016/S0022-3565(25)30726-3. PMID 994022.
  4. ^ Page Module:Citation/CS1/styles.css has no content.Wong DT, Molloy BB, Bymaster FP (January 1977). "Blockade of monoamine uptake by 1-amino-4-phenylbicyclo(2,2,2)octane (EXP 561) in rat brain and heart". Neuropharmacology. 16 (1): 11–15. doi:10.1016/0028-3908(77)90040-5. PMID 834358. S2CID 44365500.
  5. ^ a b Page Module:Citation/CS1/styles.css has no content.Maj J, Skuza G, Sowińska H, Nowak G (1987). "Pharmacological properties of EXP 561, a potential antidepressant drug". Journal of Neural Transmission. 70 (1–2): 81–97. doi:10.1007/BF01252511. PMID 2822850. S2CID 23469131.
  6. ^ Page Template:Citation/styles.css has no content.US 3308160, Snyder JA, "4-Phenylbicyclo[2.2.2]octane-1-amines and salts thereof", issued Script error: No such module "auto date formatter"., assigned to EIDP Inc. 
  7. ^ Page Module:Citation/CS1/styles.css has no content.Davis JM (1970). "Theories of biological etiology of affective disorders". In Pfeiffer CC, Smythies JR (eds.). International Review of Neurobiology. Vol. 12. pp. 145–175. doi:10.1016/s0074-7742(08)60060-4. ISBN 978-0-12-366812-7. PMID 4918142.
  8. ^ Page Module:Citation/CS1/styles.css has no content.Lehmann HE, Ban TA, Debow SL (June 1967). "A clinical-pharmacological study with EXP 561". Current Therapeutic Research, Clinical and Experimental. 9 (6): 306–308. PMID 4963065.
  9. ^ Page Module:Citation/CS1/styles.css has no content.Gershon S, Hekimian LJ, Floyd A (February 1968). "Non-correlation of preclinical-clinical evaluation of a prosposed anti-depressant 4-phenyl-bicyclo(2,2,2)octan-1-amine hydrochloride monohydrate (EXP 561)". Arzneimittel-Forschung. 18 (2): 243–245. PMID 5695389.
  10. ^ Page Module:Citation/CS1/styles.css has no content.Ross SB, Kelder D (May 1979). "Inhibition of 3H-dopamine accumulation in reserpinized and normal rat striatum". Acta Pharmacologica et Toxicologica. 44 (5): 329–335. doi:10.1111/j.1600-0773.1979.tb02339.x. PMID 474143.
  11. ^ Page Module:Citation/CS1/styles.css has no content.Carenini G, Carissimi M, D'Ambrosio R, Grumelli E, Milla E, Ravenna F (1973). "[Phenylcyclohexylamine and derivatives. IV. Salts of trans-4-phenylcyclohexylamine with -substituted 4-diphenyl- and 4-cyclohexylphenyl acetic acids and their pharmacological activity]". Il Farmaco; Edizione Scientifica. 28 (4): 265–277. PMID 4698884.
  12. ^ Page Module:Citation/CS1/styles.css has no content.Chapman, N. B., Sotheeswaran, S., Toyne, K. J. (April 1970). "Preparation of 4-substituted 1-methoxycarbonylbicyclo[2.2.2]octanes, 4-substituted 1-phenylbicyclo[2.2.2]octanes, 4-substituted 1-p-nitrophenylbicyclo[2.2.2]octanes and 1,4-disubstituted bicyclo[2.2.2]octanes". The Journal of Organic Chemistry. 35 (4): 917–923. doi:10.1021/jo00829a010.

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