Tricyanoaminopropene

Tricyanoaminopropene
Clinical data
Trade namesTriap
Legal status
Legal status
  • Investigational
Identifiers
  • 1,1,3-tricyano-2-amino-1-propene
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.011.616
Chemical and physical data
FormulaC6H4N4
Molar mass132.126 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] The drug causes a temporary hypothyroidism syndrome which resolves once 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 anti-thyroid hormone effects.[10]

It is unknown if this drug is actually safe or effective in humans.

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.
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