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| Clinical data | |
|---|---|
| Other names | 4-Hydroxytryptamine; 3-(2-Aminoethyl)-1H-indol-4-ol; UNII-DP0D1701D1 |
| Routes of administration | Oral, Intravenous |
| Pharmacokinetic data | |
| Metabolism | MAO, others |
| Metabolites | 4-HIAA |
| Excretion | urine, feces |
| Identifiers | |
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| CAS Number | |
| PubChem CID | |
| ChemSpider | |
| UNII | |
| KEGG | |
| ChEBI | |
| ChEMBL | |
| Chemical and physical data | |
| Formula | C10H12N2O |
| Molar mass | 176.219 g·mol−1 |
| 3D model (JSmol) | |
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| Names | |
|---|---|
| IUPAC name
3-(2-aminoethyl)-1H-indol-4-ol
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| Other names
4-Hydroxytryptamine; 3-(2-Aminoethyl)-1H-indol-4-ol; UNII-DP0D1701D1
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| KEGG | |
PubChem CID
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| Properties | |
| C10H12N2O | |
| Molar mass | 176.218 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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4-Hydroxytryptamine or 4-HT is a monoamine of the tryptamine class. It occurs in psilocybin-mushrooms as a necessary chemical precursor for the biosythesis of psilocybin, psilocin, baeocystin, norbaeocystin and aeruginascin[1]. It is converted into these different compounds through a range of enzymes in psilocybin mushrooms, such as 4-hydroxytryptamine kinase found in psilocybe cubensis[1]. It is a structural analog as well an isomer of serotonin, differening by the hydroxy-group being on the 4th position on the tryptamine structure, instead of the 5th.
Possible effects
editThese Effects are based on a small study from 1960 using one „intact“ cat, one „spinal“ cat, one dog and a rat[2]
- Blood pressure: Cat, 4-HT (100µg/kg i.v.) produced a rise in blood pressure 2-6 times less intense but more sustained than the same dose of 5-HT.
- Respiration: Dog, 3-4µg/kg i.v. of 5-HT caused a transitory stimulation of respiration, eventually followed by hypopnea. 4-HT required a higher dosage than 5-HT and result was always respiratory depression. Cat, both 5-HT and 4-HT caused bronchospasm. Effects of 4-HT at 100µg/kg i.v. were 2-4 times less intense but lasted longer than that caused by 5-HT.
- Dog urinary bladder: Stimulant action of 4-HT was approximately 2 times less intense than that of 5-HT, but was more sustained.
- Diuresis of hydrated rats: subcutaneous 4-HT showed only a poor antidiuretic effect. 6mg/kg were less effective than 0.04mg/kg 5-HT1.
- Nictitating membrane: 4-HT was 2-5 times less active than 5-HT in contracting the nictitating membrane of the cat. The contraction by 4-HT lasted considerably longer.
| Receptor | Rat | Human |
|---|---|---|
| 5-HTR1a | 0.095µM | - |
| 5-HTR1b | 1.05µM | - |
| 5-HTR2a | 0.725µM | - |
| 5-HTR2b | 0.725µM | - |
| 5-HTR2c | 0.725µM | 0.04µM |
Metabolism
editAfter rats were given 4-HTP, a number of metabolites were found in their urine such as 4-HT as 4-HIAA[4].
Doses of 200mg, 500mg, 1000mg DL-4-HTP produce no pharmacological effects in man[4]. 4-HIAA was the most abundant metabolite in the urine at 95-100mg after the 1000mg Dose, 53-55mg after 500mg and 22-24mg after 200mg. Only 1.3-2.2% of the administered amino acid was recovered aunchanged in the urine and less than 1% 4-HT[4].
Peaks were reached after 2 Hours at all Doses.
These results suggest that oral 4-HTP and the 4-HT originating from it are extensively metabolized by the intestinal wall and in the liver.
- ^ a b PubChem. "2.-.-.- Transferases | 2.7.-.- Transferring phosphorus-containing groups | 2.7.1.- Phosphotransferases with an alcohol group as acceptor". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-05-10.
- ^ Erspamer, V.; Glässer, A.; Mantegazzini, P. (1960-11-01). "Pharmacological actions of 4-hydroxytryptamine and 4-hydroxytryptophan". Experientia. 16 (11): 505–506. doi:10.1007/BF02158367. ISSN 1420-9071.
- ^ PubChem. "4-Hydroxytryptamine". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-05-10.
- ^ a b c Erspamer, V.; Nobili, M. B. (1961-08-01). "Observations on the fate of oral 4-hydroxytryptophan in man". Experientia. 17 (8): 351–352. doi:10.1007/BF02201756. ISSN 1420-9071.