| Stereochemistry | ABSOLUTE |
| Molecular Formula | C19H30O |
| Molecular Weight | 274.4409 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 7 / 7 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC=C[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CC[C@@]4([H])C[C@H](O)CC[C@]34C
InChI
InChIKey=KRVXMNNRSSQZJP-PHFHYRSDSA-N
InChI=1S/C19H30O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h3,9,13-17,20H,4-8,10-12H2,1-2H3/t13-,14+,15-,16-,17-,18-,19-/m0/s1
| Molecular Formula | C19H30O |
| Molecular Weight | 274.4409 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 7 / 7 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Androstenol (5α-androst-16-en-3α-ol), a pheromone that acts as a potent positive allosteric modulator of the GABA-A receptor. Androstenol was first isolated from boar testes, and several animal experiments suggest that androstenol is capable of reducing anxiety, as well as hippocampal epileptogenic activity. It was subsequently detected in humans, (primarily in males), in sweat, urine, plasma, and saliva. Androstenol is also shown to affect hormonal, behavioral and social responses in humans. In animals, androstenol has been found to produce anxiolytic-like, antidepressant-like and anticonvulsant effects.
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
PubMed
Patents
Sample Use Guides
in mice: systemic administration of androstenol (30-50 mg/kg) caused anxiolytic-like effects in mice in the open-field test and elevated zero-maze and antidepressant-like effects in the forced swim test (5-10 mg/kg).
Route of Administration:
Intraperitoneal
In whole-cell recordings from cerebellar granule cells, androstenol caused a concentration-dependent enhancement of GABA-activated currents (EC(50), 0.4 microM in cultures; 1.4 microM in slices) and prolonged the duration of spontaneous and miniature inhibitory postsynaptic currents. Androstenol (0.1-1 microM) also potentiated the amplitude of GABA-activated currents in human embryonic kidney 293 cells transfected with recombinant alpha1beta2gamma2 and alpha2beta2gamma2 GABA(A) receptors and, at high concentrations (10-300 microM), directly activated currents in these cells.
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DIASTEREOISOMER -> DIASTEREOISOMER |
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