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Phenatine

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Phenatine
Clinical data
Trade namesFenatine
Other namesPhenatin; Fenatin; Fenatine; Nicotinoylamphetamine; N-Nicotinoylamphetamine; N-Nicotinoyl-β-phenylisopropylamine; N-(α-Methylphenethyl)nicotinamide
Drug classPsychostimulant; Amphetamine
Identifiers
  • N-(1-phenylpropan-2-yl)pyridine-3-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC15H16N2O
Molar mass240.306 g·mol−1
3D model (JSmol)
  • CC(CC1=CC=CC=C1)NC(=O)C2=CN=CC=C2
  • InChI=1S/C15H16N2O/c1-12(10-13-6-3-2-4-7-13)17-15(18)14-8-5-9-16-11-14/h2-9,11-12H,10H2,1H3,(H,17,18)
  • Key:KJRJJAZBUWXZFN-UHFFFAOYSA-N

Phenatine, or phenatin, also known as N-nicotinoylamphetamine and sold under the brand name Fenatine, is a psychostimulant of the amphetamine family which was developed and used in the Soviet Union.[1][2][3][4][5][6][7] It was used in the treatment of depression, narcolepsy, post-encephalitis sequelae, alcoholic psychoses, asthenia, and other conditions.[1][5]

Chemistry

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Phenatine is a condensation product of amphetamine (phenamine) and nicotinic acid (niacin; vitamin B3).[1][6] It was first described in the scientific literature by 1955.[8][9][10][11]

Pharmacology

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Phenatine is described as having effects analogous to those of amphetamine.[5][6] Phenatine was also said to enhance physical and mental performance.[6] However, the drug was described as being a milder stimulant than amphetamine whilst supposedly being superior to amphetamine and other stimulants in various respects.[5][6] It was claimed to be much less toxic than amphetamine, to have hypotensive rather than hypertensive effects (and hence to not be contraindicated in people with hypertension), and to have reduced rebound effects and addictive potential.[5][6]

Analogues

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An analogue is methylphenatine.[8][12][13][14] Another analogue is pyridoxiphen (pyridoxiphene; pyridoxylamphetamine), the condensation product of amphetamine and pyridoxine (vitamin B6).[5][15][16] Other relatives may include thiophenatine, propylphenamine, and phenylphenamine.[13] Further analogues of phenatine and pyridoxphen include gamofen (the condensation product of amphetamine and γ-aminobutyric acid (GABA)), alafen (the condensation product of amphetamine and β-alanine), and pabofen (p-aminobenzoylamphetamine; linkage of amphetamine and p-aminobenzoic acid (PABA), an intermediate in the biosynthesis of folic acid (vitamin B9)), all of which show distinct pharmacological activity.[17]

See also

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References

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  1. ^ a b c Jablonski S, Leonard RM (1961). Russian Drug Index. Public Health Service publication. U.S. Department of Health, Education, and Welfare, Public Health Service. p. 40. Retrieved 29 September 2024 – via National Library of Medicine (U.S.).
  2. ^ Usdin E, Efron DH (1972). Psychotropic Drugs and Related Compounds (2nd ed.). National Institute of Mental Health. p. 285. Retrieved 29 September 2024.
  3. ^ Leake CD (1958). The Amphetamines: Their Actions and Uses. A monograph in the Bannerstone Division of American lectures in pharmacology. Thomas. p. 12. Retrieved 29 September 2024.
  4. ^ Grant WM (1974). Toxicology of the Eye: Drugs, Chemicals, Plants, Venoms. Thomas. p. 804. ISBN 978-0-398-02299-0. Retrieved 29 September 2024. Phenatin (Phenatine, nicotinic acid β-phenylisopropylamide, fenatin), an antidepressant stimulatory drug is reported to have altered the ability of the human eye to discriminate between orange-red and white when 20 mg was administered experimentally.
  5. ^ a b c d e f Dange SA, Adhikari GM (1963). International Socialist Miscellany (in Italian). Vol. 1. p. 131. Retrieved 29 September 2024. [...] would have no harmful side-effects. Such a drug has been produced. The staff of the chair of pharmacology of the Kirov Medical Officers College evolved, after thorough investigations, the preparation of phenatin. As to its effect and properties, phenatin is superior to all the existing stimulators of the nervous system. It was developed by Professor Sergey Arbuzov. This preparation, says the Professor, is a condensate of phenamin with nicotinic acid (Vitamin PP). It has a mild stimulating effect and simultaneously reduces the blood pressure. It can be used by people engaged in long and strenuous work and by people suffering from hypertensive disease. The preparation excites metabolism and can therefore successfully be used in obesity and old-age asthenia. Unlike phenamin, phenatin does not lead to the exhaustion of the nervous system, granted that there is no overdosage of the preparation. Our chair has also produced certain derivatives of phenatin which likewise possess valuable qualities. For instance, there is pyridoxiphen, a product of condensation of phenamin and pyridoxine (Vitamin B6). This preparation is necessary in clinical practice for treating some of the diseases of the nervous system. We are persistently looking for even more active stimulators. [...]
  6. ^ a b c d e f Problems of Space Biology. U.S. National Aeronautics and Space Administration. [for sale by Office of Technical Services, Department of Commerce.] 1973. pp. 343–344. Retrieved 29 September 2024. Phenatine is an original Soviet drug, obtained by condensing phenamine and nicotinic acid. Phenatine is much less toxic than phenamine; It is a gentler stimulant of the central nervous system. Unlike phenamlne, the drug has a hypotensive effect (Arbuzov, 1952, 1953, 1960; Makarov, 1958, and others). In this respect it can be prescribed in those cases when phenamine is contraindicated (for example, hypertonic disease, old age, asthenic syndrome, etc.). Phenatine stimulates mental and physical efficiency. Research conducted on man (Arbuzov, 1960) established that phenatine intensifies the excitatory process with brief concentration of the inhibitory process, maintaining the equilibrium of nerve processes at a higher level. The drug can intensify activity not only of the cortex of the large hemispheres, but also the subcortex. An important aspect of the drug is that its use is not accompanied by negative aftereffects; neither have cases of addiction to phenatine been noted. [...]
  7. ^ UN International Drug Control Programme (1996). "Amphetamine-type stimulants : a global review /: prepared by UNDCP at the request of the Commission on Narcotic Drugs". UN International Drug Control Programme. Retrieved 29 September 2024. Table 2: Licit use of controlled amphetamine-type substances in the manufacture of other pharmaceuticals: AMFETAMINE ("); [...] Product: phenatine; 1971 Convention: Schedule: -; optical isomer: -; Therapeutic category/Use of product: psychostimulant; isomer that is usually used: -; Conversion cases reportd (1990-1993): - [Merck Index, 1989].
  8. ^ a b Guchok MM (1955). "K sravnitel'noi farmakologicheskoi kharakteristike fenatina i metilfenatina" [Comparative pharmacological characteristics of phenatine and methylphenatine]. Farmakologiia i Toksikologiia (in Russian). 18 (5): 17–23. PMID 13294194.
  9. ^ Krupko AI (1955). "K voprosu o vliianii promedola, fenatina i eukodala na sokratitel'nuiu deiatel'nost' matki zhivotnykh" [Effect of promedole, phenatine, and eukodal on uterine contractions in animals]. Akusherstvo I Ginekologiia (in Russian). 1: 8–13. PMID 14376293.
  10. ^ Baryshnikov II (1955). "Vliianie nekotorykh proizvodnykh fenamina i fenatina na uslovnoreflektornuiu deiatel'nost' krolikov" [Effect of certain phenamine and phenatine derivatives on conditioned reflex function in rabbits]. Zhurnal Vysshei Nervnoi Deiatelnosti imeni I P Pavlova (in Russian). 5 (4): 582–590. PMID 13268044.
  11. ^ Makarov AI (1958). "Primenenie novogo stimuliatora nervnoi sistemy fenatina v klinike nervnykh boleznei" [Clinical application in nervous system diseases of a new stimulator of the nervous system phenatine]. Zhurnal Nevropatologii I Psikhiatrii imeni S.S. Korsakova (in Russian). 58 (2): 202–203. PMID 13605130.
  12. ^ Guchok MM (1968). "Vliianie fenatina i metilfenatina na deiatel'nost' vysshikh otdelov tsentral'noĭ nervnoĭ sistemy belykh krys" [Effect of phenatine and methylphenatine on the higher nervous activity in albino rats]. Farmakologiia i Toksikologiia (in Russian). 31 (1): 3–5. PMID 4233970.
  13. ^ a b Central Intelligence Agency Office of Scientific Intelligence (9 November 1959). "Scientific Intelligence Report: Soviet Research on Radiological Safety". CIA FOIA (foia.cia.gov). Retrieved 29 September 2024. A few others have been suggested as having some therapeutic effect but this has not been shown adequately. These include [...] phenatine (benzedrine plus niacin), [...] Appendix C: Substances Investigated for Prophylactic Effect Against Irradiation: [...] phenatine [...] thiophenatine [...] propylphenamine [...] phenamine [...] methylphenatine [...] methylphenatine [...] phenylphenamine [...]
  14. ^ "N-(2-methyl-1-phenylpropan-2-yl)pyridine-3-carboxamide". PubChem. U.S. National Library of Medicine. Retrieved 29 September 2024.
  15. ^ Arbuzov SI, Smirnova SM (1964). "Simpatolitcheskoe i gipotenzivnoe de istvie piridoksifena" [Sympatholytic and hypotensive effects of pyridoxiphen]. Farmakologiia i Toksikologiia (in Russian). 27: 420–423. PMID 14193108.
  16. ^ Arbuzov SI, Gorodnik AG, Nikiforov MI (1968). "O vliianii piridoksifena na nekotorye funktsii nervnoĭ sistmey" [On the effect of pyridoxiphen on some functions of the nervous system]. Farmakologiia i Toksikologiia (in Russian). 31 (2): 152–156. PMID 5674665.
  17. ^ Aleksandrova AY, Smirnova SM (1968). "[Pharmacological characteristics of the condensation product of Fenamin [amphetamine] and γ-aminobutyric acid]" (PDF). Farmakologiya i toksikologiya. 31 (5): 525–526.
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