Tricyanoaminopropene

Last updated
Tricyanoaminopropene
Tricyanoaminopropene.svg
Clinical data
Trade names Triap
Legal status
Legal status
  • Investigational
Identifiers
  • 1,1,3-tricyano-2-amino-1-propene
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard 100.011.616 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C6H4N4
Molar mass 132.126 g·mol−1
3D model (JSmol)
  • C(C#N)C(=C(C#N)C#N)N
  • InChI=1S/C6H4N4/c7-2-1-6(10)5(3-8)4-9/h1,10H2
  • Key:BNHGNFYPZNDLAF-UHFFFAOYSA-N
   (verify)

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 [1] and in vivo. It stimulates the action of the enzyme choline acetyltransferase, resulting in increased acetylcholine production. [2] This then results in increased synthesis of RNA in many different tissues in the body. [3] However it also suppresses the production of thyroxine, causing temporary hypothyroidism which returns to normal once the drug is discontinued. [4]

Tricyanoaminopropene reduces the amnesia produced by electroconvulsive shock, [5] and animal tests suggested nootropic activity, [6] [7] [8] but no beneficial effect was found when it was tested in mentally disabled children, [9] and administration to pregnant rats actually reduced learning ability in their young because of its anti-thyroid hormone effects. [10] 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.

See also

References

  1. Paul JW, Quach TT, Duchemin AM, Schrier BK, DaVanzo JP (August 1990). "1,1,3 tricyano-2-amino-1-propene (Triap): a small molecule which mimics or potentiates nerve growth factor". Brain Research. Developmental Brain Research. 55 (1): 21–27. doi:10.1016/0165-3806(90)90101-4. PMID   2208638.
  2. Paul JW, DaVanzo JP (June 1992). "1,1,3 Tricyano-2-amino-1-propene (Triap) stimulates choline acetyltransferase activity in vitro and in vivo". Brain Research. Developmental Brain Research. 67 (2): 113–120. doi:10.1016/0165-3806(92)90212-f. PMID   1511511.
  3. Dhindsa KS, Enesco HE (1978). "Radioautographic study of the effect of malononitrile dimer on RNA synthesis in mice". Acta Anatomica. 100 (1): 44–50. doi:10.1159/000144880. PMID   899675.
  4. Dhindsa KS (1980). "Histological changes in the thyroid gland of the mouse following treatment with 1, 1, 3-tricyano-2-amino-1-propene". Acta Anatomica. 106 (4): 468–472. doi:10.1159/000145216. PMID   7386168.
  5. Essman WB (1966). "Effect of tricyanoaminopropene on the amnesic effect of electroconvulsive shock". Psychopharmacologia. 9 (5): 426–433. doi:10.1007/BF00406452. PMID   4173302. S2CID   20265191.
  6. Rahwan RG (November 1971). "The biochemical and pharmacological basis of learning and memory". Agents and Actions. 2 (3): 87–102. doi:10.1007/bf01990087. PMID   4950562. S2CID   38569933.
  7. Banfi S, Cornelli U, Fonio W, Dorigotti L (December 1982). "A screening method for substances potentially active on learning and memory". Journal of Pharmacological Methods. 8 (4): 255–263. doi:10.1016/0160-5402(82)90042-0. PMID   7154677.
  8. "Brain Boosters Revealed: The Promising Nootropic Potential Uncovered in Animal Studies". nootropicmax.com.
  9. Panzer JD, Atkinson WH (1969). "Tricyanoaminopropene (TCAP): lace of improvement of mentation in mentally retarded children". Psychosomatics. 10 (2): 136–140. doi:10.1016/S0033-3182(69)71773-X. PMID   4181970.
  10. Davenport JW (February 1970). "Cretinism in rats: enduring behavioral deficit induced by tricyanoaminopropene". Science. 167 (3920): 1007–1008. Bibcode:1970Sci...167.1007D. doi:10.1126/science.167.3920.1007. PMID   4188980. S2CID   20247454.