It07:Encefabol
Encefabol
| It07:Encefabol | ||||
|---|---|---|---|---|
| ||||
| General | ||||
| Systematic name | 4,4'-bis-hydroxymethyl-2,2'-dimethyl-5,5'-(2,3-dithia-butane-1,4-diyl)-bis-pyridin-3-ol | |||
| Other names | Encephabol, encefabol, pyritinol, pyrithioxine | |||
| Molecular formula | C16H20N2O4S2 | |||
| SMILES | CC1=C(O)C(CO)=C(CSSCC2=CN=C(C)C(O)=C2CO)C=N1 | |||
| Molar mass | 368.473 gmol-1 | |||
| CAS number | 1098-97-1 | |||
| Properties | ||||
| Melting point | 218-220o C | |||
| 3-D Structure |
| |||
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references | ||||
Encefabol®, or pyritinol is a synthetic drug, derived from vitamin B6 and patented by Merck Co., proven to be effective in senile dementia treatment.[1] It is also used by some people as smart drug, although there is only limited evidence of it's effectiveness (see below).
Pharmacological data
The compound showed some promising evidence that it increases score on Choice Reaction Time and Critical Flicker Fusion tests.[2] However, the study was not exhaustive and was conducted only on 12 individuals in a three day period, thus unambigious conclusions about nootropic properties of the compound cannot be drawn.
Studies of encefabol on mice showed that N-methyl-D-aspartate receptors were regenerated in aged mice brains.[3] The receptors tend to disintegrate in aging species, and thus the study proved possible nootropic potential of the drug by showing it works as brain anti-aging agent. It has been also proved that the drug increases blood supply to cerebral brain, hence the improvement in nerve cell metabolism.[4] A study was conducted on old rats, when encefabol wes given to them for a period of 3 months. They showed improvement in T-maze performance compared to control rats. Deceleration of brain aging were observed, as the fraction of insoluble proteins decreased in the cortex. In the brain stem, higher concentrations of serotonin and noradrenaline were also found.[5] Despite limited scientific evidence for nootropic effects, it is still being used by a small number of general public for memory improvement (see section below).
Although nootropic properties remain subject pending a rigorous scientific study, there are enough evidence of symptomatic senile dementia treatment by oral administration of the drug. One example, when patients with senile dementia, treated with encefabol in a blind study, showed improvement in their physical activity, mental power, interest and alertness.[6] A list of therapeutic uses, studies and trials can be found on PubMed[7]
Adverse effects
Several cases have been reported when encefabol uptake lead to liver malfunction. In most of the cases, pyritinol was taken along with other medicine, which might have had conflicting effects.[8] For example, an adult woman was experiencing malaise, vomiting, fever. In the hospital, abnormal results for liver function tests were obtained. 600 mg pyritinol a day have been taken for a month and she was also taking nimesulide for dysmenorrhoea. After she stopped taking pyritinol, liver function improved, and returned to normal after 9 months. Another case have seen a 41-year old man taking pyritinol daily. He had to stop after he had been admitted to the hospital with nausea, vomiting, jaundice and abnormal liver function. These side effects are inconclusive and are unique cases. It must be noted that in Europe, the drug has been used for 20 years, and only a few cases resulted in drug induced hepatitis.[9]
Use by public as a nootropic
It is being marketed as a nootropic by a number of pharmacies, for example a UK based United Pharmacies. The following text was found in their website: "Pyritinol has shown to help Attention Deficit Disorder (ADD) and is used by people of all ages to improve memory, concentration, and to enhance information processing." Interest in smart drug properties of encefabol is relatively huge in general public, as can be seen in Google groups. A number of people have asked the same question "How does the drug work, does anyone have any experience with it?" after buying the drug. Another person, known by a pseudonym LifeMirage, has claimed to have used smart drugs for 15 years. His nootropic intake also includes pyritinol, although he doesn't give an explanation, as why he included the particular drug.
Synthesis
One of the routes to pyritinol synthesis, is from a vitamin B6 derivative.[10]
References
- ↑ Fischhof PK, Saletu B, Ruther E, Litschauer G, "THERAPEUTIC EFFICACY OF PYRITINOL IN PATIENTS WITH SENILE DEMENTIA OF THE ALZHEIMER TYPE (SDAT) AND MULTIINFARCT DEMENTIA (MID)", Neuropsychobiology, 26 (1-2),pages 65,1992
- ↑ Hindmarch I, Coleston DM, Kerr JS, Neuropsychobiology, 1990-1991; 24(3): 159-64
- ↑ Hartmann H., Cohen SA., Muller WE., Neuropharmacology, 32 (2): 119-125, 1993
- ↑ Herrschaft H., Munchener Medizinische Wochenschrift, 1978, 39, 1263.
- ↑ Benesova O., Tejkalova H., Kristofikova Z., Binkova B., Michalikova S., European Journal of Pharmacology, 183 (4): 1127-1128, 1990.
- ↑ Hamouz W., Pharmatherapeutica, 1977, 1, 398.
- ↑ Pyrithioxin therapeutic use [1]
- ↑ Maria V, Albuquerque A, Loureiro A, Sousa A, Victorino R, BRITISH MEDICAL JOURNAL, 328 (7439): 572-574, 2004.
- ↑ Jaffe IA., American Journal of Medicine, 80 (3): 471-476, 1986.
- ↑ Paul B., Korytnyk W., Tetrahedron, 25, 1071-1087, 1969 [2]