Tinofedrine

Last updated

Tinofedrine
Tinofedrine.svg
Clinical data
Other namesNovocebrin; D-8955; D8955; N-(3,3-Di-3-thienyl)-2-propenyl)norephedrine; (1R,2S)-β-Hydroxy-N-(3,3-di-3-thienyl)-2-propenyl)amphetamine
Drug class Sympathomimetic; Cerebral vasodilator
Identifiers
  • (1R,2S)-2-[3,3-di(thiophen-3-yl)prop-2-enylamino]-1-phenylpropan-1-ol
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.060.415 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C20H21NOS2
Molar mass 355.51 g·mol−1
3D model (JSmol)
  • C[C@@H]([C@@H](C1=CC=CC=C1)O)NCC=C(C2=CSC=C2)C3=CSC=C3
  • InChI=1S/C20H21NOS2/c1-15(20(22)16-5-3-2-4-6-16)21-10-7-19(17-8-11-23-13-17)18-9-12-24-14-18/h2-9,11-15,20-22H,10H2,1H3/t15-,20-/m0/s1
  • Key:JQSHEDRVRBSFCZ-YWZLYKJASA-N

Tinofedrine (INN Tooltip International Nonproprietary Name; developmental code name D-8955, proposed brand name Novocebrin), also known as N-(3,3-di-3-thienyl)-2-propenyl)norephedrine, is a sympathomimetic and cerebral vasodilator of the amphetamine family which was never marketed. [1] [2] [3] [4] [5] [6] It is a derivative of norephedrine and an analogue of related agents like oxyfedrine, buphenine (nylidrin), and isoxsuprine. [4] The drug was first described in the literature by 1978. [1] [6]

Related Research Articles

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<span class="mw-page-title-main">Norfenefrine</span> Sympathomimetic drug

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Racefemine, sold under the brand names Dysmalgine and Evalgin, is a uterine spasmolytic and muscle relaxant of the amphetamine family. It is the racemic threo form of dextrofemine. The drug acts as a β-adrenergic receptor agonist and sympathomimetic. It appears to no longer be marketed. Other tocolytics with similar chemical structures as phenethylamines or amphetamines include bedoradrine, buphenine, fenoterol, hexoprenaline, isoxsuprine, ritodrine, and terbutaline.

<span class="mw-page-title-main">Bufenadrine</span> Chemical compound

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<span class="mw-page-title-main">Norbudrine</span> Sympathomimetic drug

Norbudrine, also known as norbutrine or as N-cyclobutylnoradrenaline, is a drug of the phenethylamine and catecholamine families described as a sympathomimetic and bronchodilator which was never marketed. It is the N-cyclobutyl analogue of norepinephrine (noradrenaline). The drug was first described in the literature by 1966.

<span class="mw-page-title-main">Trecadrine</span> Anti-ulcer drug

Trecadrine is a drug that was originally developed as an anti-ulcer agent but was found to act as a β3-adrenergic receptor agonist with potential anti-obesity and anti-diabetic properties. It is selective for the β3-adrenergic receptor, lacking activity at the β1- and β2-adrenergic receptors. The drug is orally active. Structurally, trecadrine is a substituted β-hydroxyamphetamine and derivative of β-hydroxy-N-methylamphetamine with a tricyclic moiety attached at the amine.

<span class="mw-page-title-main">Clorprenaline</span> Bronchodilator

Clorprenaline, also known as isoprophenamine and known as clorprenaline hydrochloride in the case of the hydrochloride salt, is a sympathomimetic and bronchodilator medication which is marketed in Japan. It acts as a β-adrenergic receptor agonist or as a β-sympathomimetic. Brand names of clorprenaline in Japan are numerous and include Asnormal, Bazarl, Bronchon, Clopinerin, Conselt, Cosmoline, Fusca, Kalutein, Pentadoll, Restanolon, and Troberin. The drug was first described in the literature by 1956.

References

  1. 1 2 Elks J (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 1205. ISBN   978-1-4757-2085-3 . Retrieved 17 October 2024.
  2. Milne GW (2002). Drugs: Synonyms and Properties. Wiley. p. 730. ISBN   978-0-566-08491-1 . Retrieved 17 October 2024.
  3. "-drine sympathomimetics" (PDF). The use of stems in the selection of International Nonproprietary Names (INN) for pharmaceutical substances 2018 (Stem Book 2018). World Health Organization.
  4. 1 2 Braestrup C (2012). Psychotropic Agents: Part II: Anxiolytics, Gerontopsychopharmacological Agents, and Psychomotor Stimulants. Handbook of Experimental Pharmacology. Springer Berlin Heidelberg. p. 420. ISBN   978-3-642-67767-0 . Retrieved 17 October 2024.
  5. Knezevic S (1988). Handbook of Regional Cerebral Blood Flow. Neuropsychology and Neurolinguistics Series. L. Erlbaum Associates. p. 140. ISBN   978-0-89859-558-1 . Retrieved 17 October 2024.
  6. 1 2 Merory J, Du Boulay GH, Marshall J, Morris J, Russell RW, Symon L, et al. (October 1978). "Effect of tinofedrine (Homburg D8955) on cerebral blood flow in multi-infarct dementia". Journal of Neurology, Neurosurgery, and Psychiatry. 41 (10): 900–902. doi:10.1136/jnnp.41.10.900. PMC   493190 . PMID   731238.