Tricyanoaminopropene

Drugbox
IUPAC_name = 2-aminoprop-1-ene-1,1,3-tricarbonitrile


CAS_number = 868-54-2
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PubChem = 13356
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C=6 | H=4 | N=4
molecular_weight = 132.123 g/mol
smiles = C(C#N)C(=C(C#N)C#N)N
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Tricyanoaminopropene (TRIAP, TCAP, Malononitrile Dimer, 1,1,3-tricyano-2-amino-1-propene) is a nootropic drug which mimics the function of nerve growth factor and increases the growth of nerves and tissue regeneration both in isolated tissues [Paul JW, Quach TT, Duchemin AM, Schrier BK, DaVanzo JP. 1,1,3 tricyano-2-amino-1-propene (Triap): a small molecule which mimics or potentiates nerve growth factor. "Brain Research. Developmental Brain Research". 1990 Aug 1;55(1):21-7. PMID 2208638] and "in vivo". It stimulates the action of the enzyme choline acetyltransferase, resulting in increased acetylcholine production. [Paul JW, DaVanzo JP. 1,1,3 Tricyano-2-amino-1-propene (Triap) stimulates choline acetyltransferase activity in vitro and in vivo. "Brain Research. Developmental Brain Research". 1992 Jun 19;67(2):113-20. PMID 1511511] This then results in increased synthsis of RNA in many different tissues in the body. [Dhindsa KS, Enesco HE. Radioautographic study of the effect of malononitrile dimer on RNA synthesis in mice. "Acta Anatomica (Basel)". 1978;100(1):44-50. PMID 899675] However it also suppresses the production of thyroxine, causing temporary hypothyroidism which returns to normal once the drug is discontinued. [Dhindsa KS. Histological changes in the thyroid gland of the mouse following treatment with 1, 1, 3-tricyano-2-amino-1-propene. "Acta Anatomica (Basel)". 1980;106(4):468-72. PMID 7386168]

Tricyanoaminopropene reduces the amnesia produced by electroconvulsive shock, [Essman WB. Effect of tricyanoaminopropene on the amnesic effect of electroconvulsive shock. "Psychopharmacology (Berlin". 1966 Jan;9(5):426-433 doi|10.1007/BF00406452.] and animal tests suggested nootropic activity, [Rahwan RG. The biochemical and pharmacological basis of learning and memory. "Inflammation Research". 1971 Aug;2(2):87-102.] [Banfi S, Cornelli U, Fonio W, Dorigotti L. A screening method for substances potentially active on learning and memory. "Journal of Pharmacological Methods". 1982 Dec;8(4):255-63. PMID 7154677] [ [http://stinet.dtic.mil/oai/oai?verb=getRecord&metadataPrefix=html&identifier=AD0660565 STUDIES OF THE EFFECTS OF MANIPULATION OF BRAIN METABOLISM ON LEARNING. I. VITAMIN B12. II. MAGNESIUM PEMOLINE (CYLERT). III. MALONONITRILE DIMER (U9189). IV. ANODAL POLARIZATION.] ] but no beneficial effect was found when it was tested in retarded children, [Panzer JD, Atkinson WH. Tricyanoaminopropene (TCAP): Lack of Improvement of Mentation in Mentally Retarded Children. "Psychosomatics". 1969 Mar-Apr;10(2):136-40. PMID 4181970] and administration to pregnant rats actually reduced learning ability in their young because of its anti-thyroid hormone effects. [Davenport JW. Cretinism in Rats: Enduring Behavioral Deficit Induced by Tricyanoaminopropene. "Science" 1970 Feb;167(3920):1007-1009.] This drug thus produces two effects which oppose each other, with the nootropic effect from the increased acetylcholine production cancelled out by the opposite effect produced by the decrease in production of thyroxine. It is not known whether the efficacy of the drug could be improved by supplementation with additional thyroxine or equivalent drugs.

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