Pregna-4,20-dien-3,6-dione

Last updated
Pregna-4,20-dien-3,6-dione
Pregnadiendione structure.png
Clinical data
Other namesPregna-4,20-diene-3,6-dione
ATC code
  • None
Identifiers
  • (8S,9S,10R,13R,14S,17R)-17-ethenyl-10,13-dimethyl-2,7,8,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-3,6-dione
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
Formula C21H28O2
Molar mass 312.453 g·mol−1
3D model (JSmol)
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2C=C)CC(=O)C4=CC(=O)CC[C@]34C
  • InChI=1S/C21H28O2/c1-4-13-5-6-16-15-12-19(23)18-11-14(22)7-9-21(18,3)17(15)8-10-20(13,16)2/h4,11,13,15-17H,1,5-10,12H2,2-3H3/t13-,15-,16-,17-,20+,21+/m0/s1
  • Key:CNHWGARUXXETPK-SMWYYAGTSA-N

Pregnadienedione (PDD), or pregna-4,20-dien-3,6-dione, is a steroid and pherine, or synthetic pheromone. [1] [2] PDD has been found to activate the vomeronasal organ in men. [1] [2] Moreover, inhalation by men has been found to affect autonomic and central function and to lower luteinizing hormone and testosterone levels, while inhalation by women has few or no effects. [1] [2]

Contents

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Related Research Articles

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A steroid is an organic compound with four fused rings arranged in a specific molecular configuration.

<span class="mw-page-title-main">Vomeronasal organ</span> Smell sense organ above the roof of the mouth

The vomeronasal organ (VNO), or Jacobson's organ, is the paired auxiliary olfactory (smell) sense organ located in the soft tissue of the nasal septum, in the nasal cavity just above the roof of the mouth in various tetrapods. The name is derived from the fact that it lies adjacent to the unpaired vomer bone in the nasal septum. It is present and functional in all snakes and lizards, and in many mammals, including cats, dogs, cattle, pigs, and some primates. Humans may have physical remnants of a VNO, but it is vestigial and non-functional.

A chemoreceptor, also known as chemosensor, is a specialized sensory receptor which transduces a chemical substance to generate a biological signal. This signal may be in the form of an action potential, if the chemoreceptor is a neuron, or in the form of a neurotransmitter that can activate a nerve fiber if the chemoreceptor is a specialized cell, such as taste receptors, or an internal peripheral chemoreceptor, such as the carotid bodies. In physiology, a chemoreceptor detects changes in the normal environment, such as an increase in blood levels of carbon dioxide (hypercapnia) or a decrease in blood levels of oxygen (hypoxia), and transmits that information to the central nervous system which engages body responses to restore homeostasis.

<span class="mw-page-title-main">Dihydrotestosterone</span> Human hormone

Dihydrotestosterone is an endogenous androgen sex steroid and hormone primarily involved in the growth and repair of the prostate and the penis, as well as the production of sebum and body hair composition.

<span class="mw-page-title-main">Olfactory system</span> Sensory system used for smelling

The olfactory system, is the sensory system used for the sense of smell (olfaction). Olfaction is one of the special senses directly associated with specific organs. Most mammals and reptiles have a main olfactory system and an accessory olfactory system. The main olfactory system detects airborne substances, while the accessory system senses fluid-phase stimuli.

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<span class="mw-page-title-main">Sex hormone-binding globulin</span> Human glycoprotein that binds to androgens and estrogens

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<span class="mw-page-title-main">Nandrolone decanoate</span> Anabolic steroid

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<span class="mw-page-title-main">Neurosteroid</span> Compounds that affect neuronal excitability through modulation of specific ionotropic receptors

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<span class="mw-page-title-main">Tibolone</span> Chemical compound

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<span class="mw-page-title-main">Trestolone</span> Chemical compound

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<span class="mw-page-title-main">Androstadienone</span> Chemical compound

Androstadienone, or androsta-4,16-dien-3-one, is a 16-androstene class endogenous steroid that has been described as having potent pheromone-like activities in humans. The compound is synthesized from androstadienol by 3β-hydroxysteroid dehydrogenase, and can be converted into androstenone by 5α-reductase, which can subsequently be converted into 3α-androstenol or 3β-androstenol by 3-ketosteroid reductase.

<span class="mw-page-title-main">PHF16</span> Protein-coding gene in the species Homo sapiens

Protein Jade-3 is a protein that in humans is encoded by the PHF16 gene.

<span class="mw-page-title-main">Epiandrosterone</span> Chemical compound

Epiandrosterone, or isoandrosterone, also known as 3β-androsterone, 3β-hydroxy-5α-androstan-17-one, or 5α-androstan-3β-ol-17-one, is a steroid hormone with weak androgenic activity. It is a metabolite of testosterone and dihydrotestosterone (DHT). It was first isolated in 1931, by Adolf Friedrich Johann Butenandt and Kurt Tscherning. They distilled over 17,000 litres of male urine, from which they got 50 milligrams of crystalline androsterone, which was sufficient to find that the chemical formula was very similar to estrone.

Odour is sensory stimulation of the olfactory membrane of the nose by a group of molecules. Certain body odours are connected to human sexual attraction. Humans can make use of body odour subconsciously to identify whether a potential mate will pass on favourable traits to their offspring. Body odour may provide significant cues about the genetic quality, health and reproductive success of a potential mate.

<span class="mw-page-title-main">Fasedienol</span> Chemical compound

Fasedienol, also known as 4-androstadienol or as 4,16-androstadien-3β-ol, is a pherine which is under development by VistaGen Therapeutics in a nasal spray formulation (PRN) for the acute treatment of social anxiety disorder. It is also being investigated by VistaGen Therapeutics for the treatment of generalized anxiety disorder (GAD) and post-traumatic stress disorder (PTSD). The pherine is a positional isomer of the endogenous pheromone androstadienol. As of 2020, it is in phase III clinical trials for social anxiety disorder.

Pherines, also known as vomeropherines, are odorless synthetic neuroactive steroids that engage nasal chemosensory receptors and induce dose-dependent and reversible pharmacological and behavioral effects. Pherines target human chemosensory receptors and possibly other receptors such as the GABAA receptor and influence central nervous system activity.

No study has led to the isolation of true human sex pheromones, although various researchers have investigated the possibility of their existence.

References

  1. 1 2 3 Hayes W (2003). "Human pheromones: have they been demonstrated?". Behavioral Ecology and Sociobiology. 54 (2): 89–97. doi:10.1007/s00265-003-0613-4. S2CID   37400635.
  2. 1 2 3 Monti-Bloch L, Diaz-Sanchez V, Jennings-White C, Berliner DL (April 1998). "Modulation of serum testosterone and autonomic function through stimulation of the male human vomeronasal organ (VNO) with pregna-4,20-diene-3,6-dione". The Journal of Steroid Biochemistry and Molecular Biology. 65 (1–6): 237–242. doi:10.1016/S0960-0760(98)00025-9. PMID   9699878. S2CID   32805290.

Further reading