Beta-AndrostANOL (BANOL) Pheromone Molecule
5α-ANDROSTAN-3β-OL (Beta Androstanol) is a steroid hormone molecule first discovered and introduced as a pheromone in 1998 by the famous Salk Institute. It is a metabolite of testosterone, a cousin of Androsterone and chemically related to androgen. Androgen is a sex hormone that stimulates the normal development of sex organs in men as well as other secondary sexual characteristics.
While nearly every steroid hormone categorized as a pheromone can be linked to mood regulation, by an increasing constituent of researchers and scientists, Beta Androstanol is the only hormone that stops or reverses gene activity. It was postulated in several additional studies that this unique pheromone molecule is indicative of a as yet unclassified neurological influence not directly associated with olfaction.
Our pheromoneXS community researchers have revealed results conducive to both men and women characteristic of uplifting moods, social comfort and ease, internal peace and increased confidence. When worn by a man in the presence of a women Beta Androstanol has been demonstrated to show attractiveness.
This pheromone molecule, typically classified in the social unisexy spectrum, has many tantalizing aspects yet to be discovered. While some researchers have indicated an aggressive front with dosages as low as 2.5 mcg per spray, this effect is uncommon but worthy of mention. Most pheromone enthusiasts and hobbyists suggest dosages anywhere from 12.5 mcg up to as high as 100 mcg.
We encourage everyone to research Beta Androstanol as a fascinating and diverse pheromone molecule sure to please. At pheromoneXS we love and adore this molecule for its versatility and use it in many blends. Try it - you're going to love it.
pheromoneXS Beta-AndrostANOL is available in 10 ml or 30 ml bottles as multiple different concentrations which you can select from 12.5 mcg per spray up to 500 mcg per spray. Bottles come with Perfumers Alcohol (SD40B) as diluent time set with 10% Dipropylene Glycol (DPG). Whichever strength you select, you are sure to get the full potential of the pheromone molecule. Perfectly blended pheromone mixes are now in your control enabling you to effortlessly create your own pheromone masterpiece.
10 and 30 ml Spray Bottle with atomizer, custom designed to your concentration specifications, will produce approximately: 10ml = 80 sprays / 30ml = 240 sprays. Each bottle consists of Beta-AndrostANOL pheromone molecule in solution of 90% Perfumers Alcohol (SD40B) with 10% Dipropylene Glycol (DPG) and are ready for immediate use.
Each spray will contain the requested dosage with a possible differential of up to +/- 6%
You agree that by ordering any Pheromone Molecules you are ordering a custom product made specifically for you. This process requires lab time and can add 3-5 business days (Monday through Friday excluding holidays) to your order processing times. pheromoneXS strives to exceed customer expectations, but you should expect possible delays when ordering these. Please consider this when ordering retail and custom products together.
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Carcinogenesis. 2003 Jun;24(6):1059-65. Epub 2003 Apr 24.
Sex difference in the proliferative response of mouse hepatocytes to treatment with the CAR ligand, TCPOBOP.
Ledda-Columbano GM1, Pibiri M, Concas D, Molotzu F, Simbula G, Cossu C, Columbano A.
The nuclear receptor Constitutive Androstane Receptor (CAR) binds DNA as a heterodimer with the retinoic-X receptor and activates gene transcription. Previously, in vitro studies have shown that the testosterone metabolites, androstenol and androstenol, inhibit the constitutive transcriptional activity of CAR, suggesting that differences might exist in the response to CAR-mediated gene activation between different sexes. In this study, we have analyzed the response of female and male CD-1 mice to stimulation of hepatocyte proliferation caused by the CAR ligand TCPOBOP. Results showed that the labelling index of female hepatocytes at 24, 30 and 36 h after treatment was much higher than that found in males. The higher proliferative activity of female hepatocytes was associated with increased hepatic levels of cyclin D1, cyclin A, E2F and enhanced phosphorylation of pRb and p107. The increased mitogenic response of females was associated with higher mRNA levels of CYP2B10, a known target of CAR. Administration of androstenol to TCPOBOP-treated mice caused a reduction of labelling index, which was accompanied by a decrease of CYP2B10 and CAR mRNA levels. In conclusion, the results show that, in addition to microsomal detoxification, another biological response elicited by the CAR ligand TCPOBOP, namely, hepatocyte proliferation, occurs at higher levels in female than male mice, suggesting that CAR transcriptional activity in males is partially counteracted by physiological higher levels of testosterone metabolites such as androstenol and androstenol.
Brain Behav Evol. 2013;81(3):194-202. doi: 10.1159/000350589. Epub 2013 May 22.
Pheromone exposure influences preoptic arginine vasotocin gene expression and inhibits social approach behavior in response to rivals but not potential mates.
Mangiamele LA1, Keeney AD, D'Agostino EN, Thompson RR.
The nonapeptides arginine vasotocin (AVT) and vasopressin mediate a variety of social behaviors in vertebrates. However, the effects of these peptides on behavior can vary considerably both between and within species. AVT, in particular, stimulates aggressive and courtship responses typical of dominant males in several species, although it can also inhibit social interactions in some cases. Such differential effects may depend upon AVT influences within brain circuits that differ among species or between males that adopt alternative reproductive phenotypes and/or upon the differential activation of those circuits in different social contexts. However, to date, very little is known about how social stimuli that promote alternative behavioral responses influence AVT circuits within the brain. To address this issue, we exposed adult male goldfish to androstenedione (AD), a pheromonal signal that is released by both males and females during the breeding season, and measured social approach responses of males towards same- and other-sex individuals before and after AD exposure. In a second experiment, we measured AD-induced AVT gene expression using in situ hybridization. We found that brief exposure to AD induces social avoidance in response to rival males, but does not affect the level of sociality exhibited in response to sexually receptive females. Exposure to AD also increases AVT gene expression in the preoptic area of male goldfish, particularly in the parvocellular population of the preoptic nucleus. Together, these data suggest that AD is part of a social signaling system that induces social withdrawal specifically during male-male interactions by activating AVT neurons.
Copyright © 2013 S. Karger AG, Basel.
J Steroid Biochem Mol Biol. 1992 Nov;43(6):549-56.
GC-MS studies of 16-androstenes and other C19 steroids in human semen.
Kwan TK1, Trafford DJ, Makin HL, Mallet AI, Gower DB.
Human semen was examined for the presence of 16-androstenols, 16-androstenones and androgens. Extracts were analysed by gas chromatography-mass spectrometry after derivatization of steroids under study. In a qualitative study, 5 alpha-androst-16-en-3 alpha- and 3 beta-ols, 5,16-androstadien-3 beta-ol and 5 alpha-androstan-3 beta-ol were detected in a semen pool A. Hydroxyl groups were converted to tert-butyldimethylsilyl ethers, the ions selected for monitoring being [M-57]+, consistent with loss of the tert-butyl group. For a more detailed quantitative study, a second semen pool B was used. In this case, all hydroxyl groups were converted to trimethylsilyl ethers, while oxo groups were not derivatized. As with semen pool A, separation of steroids was achieved using capillary gas chromatography with appropriate temperature programming. Quantification was carried out by mass spectrometry using selected ion monitoring of two significant ions and appropriate internal standards. The following steroids were identified at the concentrations indicated: 5 alpha-androst-16-en-3 alpha- and 3 beta-ols and 5,16-androstadien-3 beta-ol (concentration range, 0.5-0.7 ng/ml). 5 alpha-Androst-16-en-3-one and 4,16-androstadien-3-one were also present at levels of 0.7-0.9 ng/ml. Two androgens, testosterone and 5 alpha-dihydrotestosterone were found at concentrations of 0.5 and 0.3 ng/ml, respectively. These data, showing the presence of 16-androstenes and androgens in human semen, appear to be consistent with testicular formation of these steroids. The possible significance of the odorous 16-androstenes is discussed.
J Steroid Biochem Mol Biol. 1994 Mar;48(4):409-18.
Comparison of 16-androstene steroid concentrations in sterile apocrine sweat and axillary secretions: interconversions of 16-androstenes by the axillary microflora--a mechanism for axillary odour production in man?
Gower DB1, Holland KT, Mallet AI, Rennie PJ, Watkins WJ.
The concentrations of five 16-androstene steroids were determined, by a GC-MS method, in freshly-produced apocrine sweat (adrenaline-induced), in 8 men and 2 women. The ranges of concentrations (nmol/microliter) in apocrine sweat were: 5 alpha-androst-16-en-3-one (5 alpha-A), 0.1-2.0 and 4,16-androstadien-3-one (androstadienone), 0-1.9, 5,16-Androstadien-3 beta-ol (androstadienol) was also found in 5 of the subjects (range 0.05-1.05). 5 alpha-Androst-16-en-3 alpha- or 3 beta-ols [3 alpha (beta)-androstenols] were only found in small amounts (< 0.1 nmol/microliters) in a few subjects. In the second study, prior to apocrine sweat collection (adrenaline injection), the axillary skin of 6 of the male subjects was washed with diethyl ether on an adjacent site of the axillary vault. The concentrations of 16-androstenes were compared in the ethereal extracts and apocrine sweat. The former contained detectable levels (pmol/cm2) of androstadienone (17.9 +/- 2.4), 3 alpha-androstenol (6.9 +/- 3.7), 3 beta-androstenol (1.8 +/- 1.0) and androstadienol (1.9 +/- 0.5) (means +/- SEM) in all 6 subjects. All but 1 subject also had 5 alpha-androstenone, the mean value for the others being 2.5 +/- 0.6. The axillary skin levels of 3 alpha- and 3 beta-androstenols, androstadienol and, in 3 subjects, androstadienone exceeded those in the apocrine sweat obtained from the same subjects, whereas levels of 5 alpha-androstenone in the skin extracts were all lower than in apocrine sweat samples, when related to the corresponding areas of skin sampled. The metabolism of 16-androstenes was studied in vitro in the presence of two aerobic coryneform bacteria, previously shown to metabolize testosterone as well as being capable of producing odour from extracts of axillary sweat in an odour-generation test. Although both coryneforms caused complex metabolic reactions and were capable of oxidation or reduction at C-3 and C-4, the overall direction favoured reduction. For example, large quantities of the more odorous 5 alpha-androstenone and 3 alpha-androstenol were formed from androstadienol and androstadienone. In contrast, strains of corynebacteria, unable to produce odour and incapable of metabolizing testosterone, were also unable to metabolize 16-androstenes.(ABSTRACT TRUNCATED AT 400 WORDS)
Nature. 1998 Oct 8;395(6702):612-5.
Androstane metabolites bind to and deactivate the nuclear receptor CAR-beta.
Forman BM1, Tzameli I, Choi HS, Chen J, Simha D, Seol W, Evans RM, Moore DD.
The orphan receptor CAR-beta binds DNA as a heterodimer with the retinoid-X receptor and activates gene transcription in a constitutive manner. Here we show that, in contrast to the classical nuclear receptors, the constitutive activity of CAR-beta results from a ligand-independent recruitment of transcriptional co-activators. While searching for potential ligands of CAR-beta, we found that the steroids androstanol and androstenol inhibit the constitutive activity of CAR-beta. This effect is stereospecific: only 3alpha-hydroxy, 5alpha-reduced androstanes are active. These androstanes do not interfere with heterodimerization or DNA binding of CAR-beta; instead, they promote co-activator release from the ligand-binding domain. These androstane ligands are examples of naturally occurring inverse agonists that reverse transcriptional activation by nuclear receptors. CAR-beta (constitutive androstane receptor-beta), therefore, defines an unanticipated steroidal signalling pathway that functions in a manner opposite to that of the conventional nuclear receptor pathways.
J Biol Chem. 2009 Oct 30;284(44):30547-55. doi: 10.1074/jbc.M109.040964. Epub 2009 Sep 1.
Dual activities of odorants on olfactory and nuclear hormone receptors.
Pick H1, Etter S, Baud O, Schmauder R, Bordoli L, Schwede T, Vogel H.
J Biol Chem. 2009 Dec 25;284(52):36720.
We have screened an odorant compound library and discovered molecules acting as chemical signals that specifically activate both G-protein-coupled olfactory receptors (ORs) on the cell surface of olfactory sensory neurons and the human nuclear estrogen receptor alpha (ER) involved in transcriptional regulation of cellular differentiation and proliferation in a wide variety of tissues. Hence, these apparent dual active odorants induce distinct signal transduction pathways at different subcellular localizations, which affect both neuronal signaling, resulting in odor perception, and the ER-dependent transcriptional control of specific genes. We demonstrate these effects using fluorescence-based in vitro and cellular assays. Among these odorants, we have identified synthetic sandalwood compounds, an important class of molecules used in the fragrance industry. For one estrogenic odorant we have also identified the cognate OR. This prompted us to compare basic molecular recognition principles of odorants on the two structurally and apparent functionally non-related receptors using computational modeling in combination with functional assays. Faced with the increasing evidence that ORs may perform chemosensory functions in a number of tissues outside of the nasal olfactory epithelium, the unraveling of these molecular ligand-receptor interaction principles is of critical importance. In addition the evidence that certain olfactory sensory neurons naturally co-express ORs and ERs may provide a direct functional link between the olfactory and hormonal systems in humans. Our results are therefore useful for defining the structural and functional characteristics of ER-specific odorants and the role of odorant molecules in cellular processes other than olfaction.
|Documents||pheromoneXS is striving to provide our valued clients with data sheets on every named pheromone molecule we sell, so you can buy with confidence. We are continually having each molecule assayed by independent third party laboratories like Sigma-Aldrich, Steraloids and Intertek. Accessibility to this data is an ongoing project that we are committed to, however not all components have been completed yet. We appreciate your patience and understanding.|
|Empirical Formula (Hill Notation)||C19 H32 O|
|Application||5α-ANDROSTAN-3β-OL (Beta Androstanol) is a testosterone metabolite similar in chemical structure to androgen which is found in men. This steroid hormone is attributed with direct emotional responses associated with attractiveness, social comfort, internal peace, mood elevation and contrarily also linked to aggression and anger.|