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Estratetraenol (estra-1,3,5(10),16-tetraen-3-ol) is an endogenous estrane steroid (a C18 steroid built on the same carbon skeleton as the estrogens) first isolated from the urine of pregnant women in 1968. It carries an aromatic A-ring like the classical estrogens but lacks the oxygen at carbon 17, which leaves it essentially devoid of conventional estrogenic hormone activity. It is best known as a putative human chemosignal (a chemical thought to carry social information between individuals), where it is treated as the female-associated counterpart to the male-associated steroid androstadienone. A body of psychophysical and neuroimaging work reports that trace, near-odorless exposure to estratetraenol can bias perception, mood, and physiological arousal in a sexually dimorphic manner, although independent replications have been mixed and its status as a true pheromone remains contested.
- Reported in several studies to bias heterosexual men toward perceiving ambiguous human motion and gender cues as more feminine
- Associated in some experiments with sex-specific shifts in mood and in the emotional reading of biological motion
- Linked in a small number of studies to increased cooperative behavior and altered sexual cognition in men
- Studied as a probe for understanding sexually dimorphic hypothalamic responses to social odors
- No validated benefit for cognition, mood, or hormonal health outside experimental settings
Overview
An endogenous estrane steroid studied almost entirely as a putative female-associated human chemosignal rather than as a classical hormone.
- It was first isolated in 1968 from the urine of pregnant women, long before anyone proposed it as a pheromone.
- Despite having an aromatic A-ring like estradiol, it lacks the oxygen at carbon 17 and is therefore essentially non-estrogenic, so it does not act as a conventional female sex hormone.
- It is chemically an estrane (a C18 steroid), which makes it the estrogen-family counterpart to the androstane-family androstadienone with which it is almost always paired in studies.
- Because the human vomeronasal organ is vestigial and its receptor genes are largely non-functional, any signaling by estratetraenol must run through the ordinary sense of smell rather than a dedicated pheromone organ.
Mechanism
Estratetraenol has no well-established high-affinity receptor of its own, and its proposed activity is understood mainly at the level of sensory neurobiology rather than classical endocrine signaling. Structurally it is an estrane (C18 steroid) with an aromatic A-ring bearing a phenolic 3-hydroxyl group and an additional 16,17 double bond; because it lacks the 17-position oxygen that estradiol uses to anchor into the receptor, it binds the estrogen receptors (ER-alpha and ER-beta, the nuclear proteins that mediate estrogen signaling) only negligibly and is effectively non-estrogenic.
In the chemosignaling literature it is delivered as a trace odorant and is thought to be transduced by the main olfactory system (the primary smell pathway in the nose); humans do not possess a functional vomeronasal organ (a separate accessory smell organ used by many mammals for pheromones), since the human vomeronasal structures are vestigial, the relevant V1R and V2R receptor genes are largely pseudogenized, and the TRPC2 ion channel that vomeronasal neurons rely on is non-functional in people.
Functional imaging work reports that smelling estratetraenol produces activation in the anterior (a deep brain region governing hormonal and sexual physiology) that differs by the observer's sex and sexual orientation, and psychophysical studies describe sex-specific shifts in how observers judge gender, emotion, and the motion of point-light human figures.
The biosynthetic origin is not fully characterized; the aromatic A-ring implies an aromatization step, and the 16,17 unsaturation places it alongside the delta-16 steroid family (the same 16-dehydro pathway that yields the 16-androstene odor steroids), plausibly arising from delta-16 intermediates during pregnancy. No pharmacologically active human metabolites of estratetraenol have been established.
receptor fingerprint
Main olfactory epitheliumChemosensory detection of trace odorant
Anterior (functional response)Sex-specific activation on olfactory exposure
Anterior Sex- and orientation-differentiated activation on imaging
receptors (ER-alpha / ER-beta)Negligible binding; lacks the 17-oxygen needed for anchoring
Vomeronasal organNo functional signaling in humans (organ is vestigial)
receptor (ER)Weak, likely negligible agonism
VN1R1 vomeronasal-type receptor (putative)Proposed but unconfirmed ligand for steroid chemosignals
-A receptorNo established modulation
Main olfactory epithelium and olfactory receptorsChemosensory detection as a social odor cue
Microsomal epoxide hydrolase (via the 16,17-epoxide )Substrate for epoxide ring hydrolysis
Safetyrisks and cautions, not medical advice
Estratetraenol has not been evaluated in formal toxicology, chronic exposure, or systemic pharmacokinetic studies, and there is no established therapeutic or supplemental use. In human research it is applied only as a trace, near-threshold odorant, typically a small quantity dissolved in a carrier such as propylene glycol and smelled briefly, and no adverse effects have been reported at these minute concentrations. Because it is essentially non-estrogenic and is presented in vanishingly small amounts, it is not expected to exert hormonal effects through the bloodstream, but this has not been directly characterized in controlled safety trials. It should be regarded as an experimental research substance rather than a product with any validated safety profile for ingestion, topical application, or repeated use.
History
Estratetraenol was chemically identified in 1968 by Thysen, Elliott, and Katzman, who isolated it from the urine of pregnant women, establishing it as an endogenous human steroid. It attracted little attention for decades until the surge of interest in candidate human pheromones in the 1990s and 2000s, when it was paired conceptually with androstadienone (a steroid enriched in male sweat and semen) and cast as a female-associated signal.
Early mood and physiology work by Jacob and McClintock and colleagues examined steroidal chemosignals in context-dependent settings, and a widely cited 2014 study by Zhou and colleagues in Current Biology reported that estratetraenol biased gender perception in heterosexual men but not women, catalyzing a wave of follow-up experiments on cooperation, sexual cognition, emotional perception of biological motion, and interactions with intranasal oxytocin. Over the same period, critics such as Wyatt argued that the field had never met the rigorous bioassay standard used to define pheromones in other species, and controlled double-blind attempts, including work by Hare and colleagues in 2017, failed to reproduce several of the headline effects.
Reputation
Within the chemosensory and social neuroscience communities, estratetraenol is regarded as a prominent but unproven candidate human chemosignal rather than an accepted pheromone. Proponents point to a cluster of studies reporting sexually dimorphic effects on gender judgment, mood, cooperative behavior, and hypothalamic activation, while skeptics emphasize small samples, publication bias, and failed replications, and note that neither estratetraenol nor androstadienone was ever isolated through the bioassay-guided approach that defines pheromones in other animals.
Reviews by Wyatt and commentary in the chemistry press have repeatedly flagged the compound as emblematic of a field that outran its evidence. In nootropic and supplement circles it has essentially no presence, as it is not sold or used for cognitive or hormonal benefit; its reputation is almost entirely academic and centers on the open question of whether humans communicate chemically at all.
Subjective profileweighing the evidence above
Not something to take. It has no established receptor of its own, essentially no hormonal activity, and its entire literature is lab work on how men read faces and motion after smelling a trace of it. Genuinely interesting for what it suggests about social perception, and useless as a supplement.
Resources
This entry is here for reference.
Research
- 1963first cited[Biogenesis of estratetraenol in man].
- 2001controlled trialContext-dependent effects of steroid chemosignals on human physiology and mood.
- 2021most active year4 papers
- 2025most recentPrejudice, Proxemic Space, and Social Odor: The Representation of the 'Outsider' Through an Evo…
- 1.Chemosensory communication of gender through two human steroids in a sexually dimorphic manner.
- 2.Identification of estra-1,3,5(10),16-tetraen-3-ol (estratetraenol) from the urine of pregnant women (1).
- 3.Context-dependent effects of steroid chemosignals on human physiology and mood.
- 4.Human chemosignals modulate emotional perception of biological motion in a sex-specific manner.
- 5.Women's fertility cues affect cooperative behavior: Evidence for the role of the human putative chemosignal estratetraenol.
- 6.A scent of romance: human putative pheromone affects men's sexual cognition.
- 7.Estratetraenol increases preference for large sexual reward but not impulsivity among heterosexual males.
- 8.Oxytocin modulates human chemosensory decoding of sex in a dose-dependent manner.
- 9.Pheromone effects on the human hypothalamus in relation to sexual orientation and gender.
- 10.Putative sex-specific human pheromones do not affect gender perception, attractiveness ratings or unfaithfulness judgements of opposite sex faces.
- 11.The search for human pheromones: the lost decades and the necessity of returning to first principles.
- 12.Reproducible research into human chemical communication by cues and pheromones: learning from psychology's renaissance.
27 listed here; entry last updated August 2026
Reviews
My notesprivate to this device
FAQ
Is estratetraenol a proven human pheromone?
No. It is a putative or candidate chemosignal. Some studies report sexually dimorphic effects on perception and mood, but the compound was never validated through the bioassay-guided standard used to define pheromones in other species, and several key findings have not replicated.
Is estratetraenol an estrogen?
It belongs to the estrane (estrogen) family by carbon skeleton and has an aromatic A-ring, but it lacks the 17-position oxygen that classical estrogens use to bind the estrogen receptor. As a result it is essentially non-estrogenic and does not function as a conventional sex hormone.
How is estratetraenol detected by the body?
In research it is presented as a trace odorant and is thought to be sensed through the main olfactory system, the ordinary sense of smell. Humans lack a functional vomeronasal organ, the accessory smell organ many mammals use for pheromones, so no dedicated pheromone pathway is available.
Can you take estratetraenol as a supplement?
No. It is not sold or used as a supplement and has no established dosing, therapeutic use, or safety profile. It exists in the literature only as an experimental chemosignal applied in tiny amounts under laboratory conditions.
Why is it filed under androstane here?
Only as a schema limitation. Chemically it is an estrane (a C18 estrogen-family steroid), not an androstane, but it is grouped with androstadienone because the two are studied together as paired female-associated and male-associated chemosignals.
Limitations of the evidence
- Not assessed for safety with systemic, chronic, or repeated exposure
Adverse effects
- No validated benefit for cognition, mood, or hormonal health outside experimental settings
Notes and cautions
- No adverse effects characterized at the trace, near-threshold concentrations used in chemosensory research
- Reported behavioral and perceptual effects are subtle, inconsistent across laboratories, and have failed several independent replications