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10,13-dimethyl-17-oxo-3-sulfooxy-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene

Names

[ CAS No. ]:
651-48-9

[ Name ]:
10,13-dimethyl-17-oxo-3-sulfooxy-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene

[Synonym ]:
Dehydroepiandrosterone 3-sulfate
dehydroepiandrosterone 3β-sulfate
[3H]-Dehydroepiandrosterone 3-sulfate
DHEA-sulphate
ANDROST-5-EN-17-ONE,3-(SULFOOXY)-, (3B)-
dehydroepiandrosterone 3-sulphate
DHEA sulfate

Biological Activity

[Description]:

Dehydroepiandrosterone sulfate, a neuroactive neurosteroid, plays a major role in brain development and aging by influencing the migration of neurons, arborization of dendrites, and formation of new synapses[1][2][3].

[Related Catalog]:

Signaling Pathways >> Others >> Others
Research Areas >> Neurological Disease

[In Vitro]

Dehydroepiandrosterone sulfate (DHEAS) selectively increased the length of neurites containing the dendritic marker MAP-2[1]. Dehydroepiandrosterone sulfate (DHEAS) has been reported to increase neuronal excitability (firing rate) when directly applied to septal-preoptic neurons[1]. Dehydroepiandrosterone (DHEA) is produced in prodigious quantities by the humanadrenal, principally as the 3-sulfoconjugate DHEA sulfate (DS) during intrauterine life[2]. Dehydroepiandrosterone sulfate (DHEAS) is generally nontoxic and lacks adverse side effects even when it is administered chronically[3].

[In Vivo]

DHEAS chronic administration produces a dose-dependent effect on performance[3]. Animal Model: Sixty-four male Sprague-Dawley rats, approximately 90 days of age (300-400 g)[3]. Dosage: 5, 10, or 20 mg/kg. Administration: Subcutaneous injection starting 7 days post-surgery and 1 h prior to all behavioral testing. Result: Significantly effective in improving latency to reach the platform as compared to injured rats receiving vehicle.

[References]

[1]. E E Baulieu, et al. Dehydroepiandrosterone (DHEA) and dehydroepiandrosterone sulfate (DHEAS) as neuroactive neurosteroids. Proc Natl Acad Sci U S A. 1998 Apr 14;95(8):4089-91.

[2]. C R Parker Jr, et al. Dehydroepiandrosterone and dehydroepiandrosterone sulfate production in the human adrenal during development and aging. Steroids. 1999 Sep;64(9):640-7.

[3]. Stuart W Hoffman, et al. The delayed administration of dehydroepiandrosterone sulfate improves recovery of function after traumatic brain injury in rats. J Neurotrauma. 2003 Sep;20(9):859-70.

Chemical & Physical Properties

[ Density]:
1.1763 g/ml

[ Melting Point ]:
190-192 °C (lit.)

[ Molecular Formula ]:
C19H28O5S

[ Molecular Weight ]:
368.49

[ Exact Mass ]:
368.16600

[ PSA ]:
89.05000

[ LogP ]:
4.78710

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
BV8530000
CHEMICAL NAME :
Androst-5-en-17-one, 3-(sulfooxy)-, (3-beta)-
CAS REGISTRY NUMBER :
651-48-9
LAST UPDATED :
199604
DATA ITEMS CITED :
5
MOLECULAR FORMULA :
C19-H28-O5-S
MOLECULAR WEIGHT :
368.53

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
655 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
SCYYDZ Shengzhi Yu Biyun. Reproduction and Contraception. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) 1980- Volume(issue)/page/year: 13,414,1993
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
293 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
SCYYDZ Shengzhi Yu Biyun. Reproduction and Contraception. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) 1980- Volume(issue)/page/year: 13,414,1993 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Primate - monkey
DOSE/DURATION :
25200 ug/kg/28D-C
TOXIC EFFECTS :
Kidney, Ureter, Bladder - other changes in urine composition Endocrine - effect on menstrual cycle Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol)
REFERENCE :
FESTAS Fertility and Sterility. (American Fertility Soc., 608 13th Ave. S, Birmingham, AL 35282) V.1- 1950- Volume(issue)/page/year: 57,912,1992 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
12 mg/kg
SEX/DURATION :
female 39 week(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - other effects Reproductive - Effects on Newborn - biochemical and metabolic Endocrine - androgenic
REFERENCE :
NISFAY Nippon Sanka Fujinka Gakkai Zasshi. Journal of the Japan Society of Obstetrics and Gynecology. (Nippon Sanka Fujinka Gakkai Zasshi, Hoken Kaikan Bekkan, 1-1 Sadohara-cho, Ichigaya, Shijuku-ku, Tokyo 162, Japan) V.1- 1949- Volume(issue)/page/year: 41,806,1989
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
200 mg/kg
SEX/DURATION :
female 10-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - uterus, cervix, vagina Reproductive - Maternal Effects - other effects
REFERENCE :
SCYYDZ Shengzhi Yu Biyun. Reproduction and Contraception. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) 1980- Volume(issue)/page/year: 13,414,1993

Safety Information

[ Hazard Codes ]:
Xn

Precursor & DownStream


Related Compounds

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