User:BusterTheBusta/4-Hydroxytryptamine

4-Hydroxytryptamine
Names
	IUPAC name 3-(2-aminoethyl)-1H-indol-4-ol
	Other names 4-Hydroxytryptamine; 3-(2-Aminoethyl)-1H-indol-4-ol; UNII-DP0D1701D1
Identifiers
CAS Number	570-14-9;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:139217;
ChEMBL	ChEMBL18855;
ChemSpider	10823;
KEGG	C21762;
PubChem CID	11297;
	InChI InChI=1S/C10H12N2O/c11-5-4-7-6-12-8-2-1-3-9(13)10(7)8/h1-3,6,12-13H,4-5,11H2 Key: FKIRTWDHOWAQGX-UHFFFAOYSA-N;
	SMILES C1=CC2=C(C(=C1)O)C(=CN2)CCN;
Properties
Chemical formula	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). Infobox references

4-Hydroxytryptamine
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
	IUPAC name 3-(2-aminoethyl)-1H-indol-4-ol;
CAS Number	570-14-9;
PubChem CID	11297;
ChemSpider	10823;
UNII	DP0D1701D1;
KEGG	C21762;
ChEBI	CHEBI:139217;
ChEMBL	ChEMBL18855;
Chemical and physical data
Formula	C10H12N2O
Molar mass	176.219 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1=CC2=C(C(=C1)O)C(=CN2)CCN;
	InChI InChI=1S/C10H12N2O/c11-5-4-7-6-12-8-2-1-3-9(13)10(7)8/h1-3,6,12-13H,4-5,11H2; Key:FKIRTWDHOWAQGX-UHFFFAOYSA-N;

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

These 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 Binding in Ki^[3]
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

After 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.

[:0-1] 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.

[2] 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.

[3] PubChem. "4-Hydroxytryptamine". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-05-10.

[:2-4] 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.

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