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Progesterone: Difference between revisions
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>Lilylunatic Fixed citations to be consistent |
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Progesterone was first discovered in 1929 by George W. Corner and Willard M. Allen. By 1934 pure crystalline material was achieved by Adolf Butenandt at the ''Chemisches Institut of Technical University'' in Gdańsk. Synthesis was accomplished later that year. | Progesterone was first discovered in 1929 by George W. Corner and Willard M. Allen. By 1934 pure crystalline material was achieved by Adolf Butenandt at the ''Chemisches Institut of Technical University'' in Gdańsk. Synthesis was accomplished later that year. | ||
<ref name="Josimovich 2013 p. ">{{cite book | last=Josimovich | first=J.B. | title=Gynecologic Endocrinology | publisher=Springer Science & Business Media |url=https://books.google.com/books?id=9vv2BwAAQBAJ&pg=PA25 |date=11 November 2013 |publisher=Springer Science & Business Media |isbn=978-1-4613-2157-6 |pages=9, 25–29 |access-date=1 February 2016 |archive-date=14 January 2023 |archive-url=https://web.archive.org/web/20230114024947/https://books.google.com/books?id=9vv2BwAAQBAJ&pg=PA25 | date=2013-11-09 | isbn=978-1-4613-2157-6 | page=}}</ref> | <ref name="Josimovich 2013 p. ">{{cite book | last=Josimovich | first=J.B. | title=Gynecologic Endocrinology | publisher=Springer Science & Business Media |url=https://books.google.com/books?id=9vv2BwAAQBAJ&pg=PA25 |date=11 November 2013 | publisher=Springer Science & Business Media |isbn=978-1-4613-2157-6 |pages=9, 25–29 |access-date=1 February 2016 |archive-date=14 January 2023 |archive-url=https://web.archive.org/web/20230114024947/https://books.google.com/books?id=9vv2BwAAQBAJ&pg=PA25 | date=2013-11-09 | isbn=978-1-4613-2157-6 | page=}}</ref> | ||
In a 2012 study higher levels of progesterone were linked to lower affinity to competitive behavior in women.<ref name="Buser 2012 pp. 1–10">{{cite journal | last=Buser | first=Thomas | title=The impact of the menstrual cycle and hormonal contraceptives on competitiveness|journal=Journal of Economic Behavior & Organization|series=Gender Differences in Risk Aversion and Competition|volume=83|issue=1|pages=1–10|doi=10.1016/j.jebo.2011.06.006|issn=0167-2681|url=https://pure.uva.nl/ws/files/1864146/117489_376503.pdf|access-date=2 February 2024|archive-date=2 February 2024|archive-url=https://web.archive.org/web/20240202143019/https://pure.uva.nl/ws/files/1864146/117489_376503.pdf | In a 2012 study higher levels of progesterone were linked to lower affinity to competitive behavior in women.<ref name="Buser 2012 pp. 1–10">{{cite journal | last=Buser | first=Thomas | title=The impact of the menstrual cycle and hormonal contraceptives on competitiveness|journal=Journal of Economic Behavior & Organization|series=Gender Differences in Risk Aversion and Competition|volume=83|issue=1|pages=1–10|doi=10.1016/j.jebo.2011.06.006|issn=0167-2681|url=https://pure.uva.nl/ws/files/1864146/117489_376503.pdf|access-date=2 February 2024|archive-date=2 February 2024|archive-url=https://web.archive.org/web/20240202143019/https://pure.uva.nl/ws/files/1864146/117489_376503.pdf}}</ref><ref name="Piosik 2003 pp. 135–138">{{cite journal | last=Piosik | first=Romuald | title=Adolf Butenandt und sein Wirken an der Technischen Hochschule Danzig | journal=CHEMKON | volume=10 | issue=3 | date=2003 | issn=0944-5846 | doi=10.1002/ckon.200390038 | pages=135–138}}</ref> | ||
==Chemistry== | ==Chemistry== | ||
{{chemistry}} | {{chemistry}} | ||
Progesterone is a naturally occurring pregnane steroid and is also known as pregn-4-ene-3,20-dione. It has a double bond (4-ene) between the C4 and C5 positions and two ketone groups (3,20-dione), one at the C3 position and the other at the C20 position.<ref name="Pubchem">{{Cite web|date= 12 March 2024|title= Compound Summary Progesterone|publisher=National Library of Medicine|access-date=12 March 2024|url=https://pubchem.ncbi.nlm.nih.gov/compound/progesterone}}</ref> | Progesterone is a naturally occurring pregnane steroid and is also known as pregn-4-ene-3,20-dione. It has a double bond (4-ene) between the C4 and C5 positions and two ketone groups (3,20-dione), one at the C3 position and the other at the C20 position.<ref name="Pubchem">{{Cite web|date= 12 March 2024|title= Compound Summary Progesterone| publisher=National Library of Medicine|access-date=12 March 2024|url=https://pubchem.ncbi.nlm.nih.gov/compound/progesterone}}</ref> | ||
==Pharmacology== | ==Pharmacology== | ||
{{pharmacology}} | {{pharmacology}} | ||
Progesterone on it's own acts as a antagonist on the '''σ<sub>2</sub>''' receptor and as a negative allosteric modulator on nicotinic acetylcholine receptors. However most of the psychoactive effects of progesterone are induced by it's metabolites.<ref name="Gonzalez 2020 p. 1846">{{cite journal | last=Gonzalez | first=Susana Laura | title=Progesterone for the treatment of central nervous system disorders: the many signaling roads for a single molecule | journal=Neural Regeneration Research | volume=15 | issue=10 | date=2020 | issn=1673-5374 | pmid=32246629 | pmc=7513974 | doi=10.4103/1673-5374.280314 | doi-access=free | page=1846}}</ref> | Progesterone on it's own acts as a antagonist on the '''σ<sub>2</sub>''' receptor and as a negative allosteric modulator on nicotinic acetylcholine receptors. However most of the psychoactive effects of progesterone are induced by it's metabolites.<ref name="Gonzalez 2020 p. 1846">{{cite journal | last=Gonzalez | first=Susana Laura | title=Progesterone for the treatment of central nervous system disorders: the many signaling roads for a single molecule | journal=Neural Regeneration Research | volume=15 | issue=10 | date=2020 | issn=1673-5374 | pmid=32246629 | pmc=7513974 | doi=10.4103/1673-5374.280314 | doi-access=free | page=1846}}</ref> | ||
===Metabolism=== | ===Metabolism=== | ||
Progesterone is mainly metabolised in the liver, therefore the route of administration significantly influences the intensity of experienced effects. The most important metabolites are allopregnanolone, pregnanolone, isopregnanolone and epipregnanolone.<ref name="Kolatorova Vitku Suchopar Hill 2022 p. 7989">{{cite journal | last=Kolatorova | first=Lucie | last2=Vitku | first2=Jana | last3=Suchopar | first3=Josef | last4=Hill | first4=Martin | last5=Parizek | first5=Antonin | title=Progesterone: A Steroid with Wide Range of Effects in Physiology as Well as Human Medicine | journal=International Journal of Molecular Sciences | volume=23 | issue=14 | date=2022-07-20 | issn=1422-0067 | pmid=35887338 | Progesterone is mainly metabolised in the liver, therefore the route of administration significantly influences the intensity of experienced effects. The most important metabolites are allopregnanolone, pregnanolone, isopregnanolone and epipregnanolone.<ref name="Kolatorova Vitku Suchopar Hill 2022 p. 7989">{{cite journal | last=Kolatorova | first=Lucie | last2=Vitku | first2=Jana | last3=Suchopar | first3=Josef | last4=Hill | first4=Martin | last5=Parizek | first5=Antonin | title=Progesterone: A Steroid with Wide Range of Effects in Physiology as Well as Human Medicine | journal=International Journal of Molecular Sciences | volume=23 | issue=14 | date=2022-07-20 | issn=1422-0067 | pmid=35887338 | doi=10.3390/ijms23147989 | doi-access=free | page=7989}}</ref> | ||
Allopregnanolone and Pregnanolone are documented to have antidepressant, anxiolytic, stress reducing, antiagressive, sedative, sleep aiding, analgesic, amnesic, anesthetic, anticonvulsant & neuroprotective effects.<ref name="Diviccaro Cioffi Falvo Giatti 2022 p. ">{{cite journal | last=Diviccaro | first=Silvia | last2=Cioffi | first2=Lucia | last3=Falvo | first3=Eva | last4=Giatti | first4=Silvia | last5=Melcangi | first5=Roberto Cosimo | title=Allopregnanolone: An overview on its synthesis and effects | journal=Journal of Neuroendocrinology | volume=34 | issue=2 | date=2022 | issn=0953-8194 | pmid=34189791 | Allopregnanolone and Pregnanolone are documented to have antidepressant, anxiolytic, stress reducing, antiagressive, sedative, sleep aiding, analgesic, amnesic, anesthetic, anticonvulsant & neuroprotective effects.<ref name="Diviccaro Cioffi Falvo Giatti 2022 p. ">{{cite journal | last=Diviccaro | first=Silvia | last2=Cioffi | first2=Lucia | last3=Falvo | first3=Eva | last4=Giatti | first4=Silvia | last5=Melcangi | first5=Roberto Cosimo | title=Allopregnanolone: An overview on its synthesis and effects | journal=Journal of Neuroendocrinology | volume=34 | issue=2 | date=2022 | issn=0953-8194 | pmid=34189791 | doi=10.1111/jne.12996 | page=}}</ref><ref name="PubChem p788">{{cite web | title=Brexanolone | website=PubChem | url=https://pubchem.ncbi.nlm.nih.gov/compound/92786 | access-date=2024-03-12}}</ref>Allopregnanolone and Pregnanolone act as positive allosteric modulators of GABA<sub>A</sub> whereas isopregnanolone and epipregnanolone selectively counteract GABA<sub>A</sub> as well as the sedative and anesthetic effects.<ref name="Kolatorova Vitku Suchopar Hill 2022 p. 7989">{{cite journal | last=Kolatorova | first=Lucie | last2=Vitku | first2=Jana | last3=Suchopar | first3=Josef | last4=Hill | first4=Martin | last5=Parizek | first5=Antonin | title=Progesterone: A Steroid with Wide Range of Effects in Physiology as Well as Human Medicine | journal=International Journal of Molecular Sciences | volume=23 | issue=14 | date=2022-07-20 | issn=1422-0067 | pmid=35887338 | doi=10.3390/ijms23147989 | doi-access=free | page=7989}}</ref> | ||
==Subjective effects== | ==Subjective effects== | ||
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|{{effects/physical| | |{{effects/physical| | ||
If applicable, a brief paragraph summary of the substance's physical effects may be included here. | If applicable, a brief paragraph summary of the substance's physical effects may be included here. | ||
You may select physical effects to add below [[Subjective effect index#Physical effects|here]]. | You may select physical effects to add below [[Subjective effect index#Physical effects|here]]. | ||
*'''[[Effect::Higher core temperature]]''' - at high concentration progesterone elevates body temperature for ~1°C | *'''[[Effect::Higher core temperature]]''' - at high concentration progesterone elevates body temperature for ~1°C | ||
*'''[[Effect::Sedation]]''' | *'''[[Effect::Sedation]]''' | ||
*'''[[Effect::Pain relief]]''' | *'''[[Effect::Pain relief]]''' | ||
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}} | }} | ||
<!--{{effects/visual| | <!--{{effects/visual| | ||
If applicable, a brief paragraph summary of the substance's visual effects may be included here. | If applicable, a brief paragraph summary of the substance's visual effects may be included here. | ||
You may select visual effects to add below [[Subjective effect index#Visual effects|here]]. | You may select visual effects to add below [[Subjective effect index#Visual effects|here]]. | ||
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|{{effects/cognitive| | |{{effects/cognitive| | ||
If applicable, a brief paragraph summary of the substance's cognitive effects may be included here. | If applicable, a brief paragraph summary of the substance's cognitive effects may be included here. | ||
You may select from a list of cognitive effects to add below [[Subjective effect index#Cognitive effects|here]]. | You may select from a list of cognitive effects to add below [[Subjective effect index#Cognitive effects|here]]. | ||
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*'''[[Effect::Dizziness]]''' | *'''[[Effect::Dizziness]]''' | ||
*'''[[Effect::Sleepiness]]''' | *'''[[Effect::Sleepiness]]''' | ||
*'''[[Effect::Anxiety suppression]]''' | *'''[[Effect::Anxiety suppression]]''' | ||
*'''[[Effect::Physical euphoria]]''' | *'''[[Effect::Physical euphoria]]''' | ||
*'''[[Effect::Increased libido]]''' | *'''[[Effect::Increased libido]]''' | ||
*'''[[Effect::Mindfulness]]''' | *'''[[Effect::Mindfulness]]''' | ||
}} | }} | ||
<!--{{effects/auditory| | <!--{{effects/auditory| | ||
If applicable, a brief paragraph summary of the substance's auditory effects may be included here. | If applicable, a brief paragraph summary of the substance's auditory effects may be included here. | ||
You may select from a list of auditory effects to add below [[Subjective effect index#Auditory effects|here]]. | You may select from a list of auditory effects to add below [[Subjective effect index#Auditory effects|here]]. | ||
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}}--> | }}--> | ||
<!--{{effects/multisensory| | <!--{{effects/multisensory| | ||
If applicable, a brief paragraph summary of the substance's multisensory effects may be included here. | If applicable, a brief paragraph summary of the substance's multisensory effects may be included here. | ||
You may select from a list of multisensory effects to add below [[Subjective effect index#Multisensory effects|here]]. | You may select from a list of multisensory effects to add below [[Subjective effect index#Multisensory effects|here]]. | ||
*'''[[Effect::Multisensory effect1]]''' | *'''[[Effect::Multisensory effect1]]''' | ||
*'''[[Effect::Multisensory effect2]]''' | *'''[[Effect::Multisensory effect2]]''' | ||
}}--> | }}--> | ||
<!--{{effects/transpersonal| | <!--{{effects/transpersonal| | ||
If applicable, a brief paragraph summary of the substance's transpersonal effects may be included here. | If applicable, a brief paragraph summary of the substance's transpersonal effects may be included here. | ||
You may select from a list of transpersonal effects to add below [[Subjective effect index#Transpersonal effects|here]]. | You may select from a list of transpersonal effects to add below [[Subjective effect index#Transpersonal effects|here]]. | ||
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It is strongly recommended that one use [[harm reduction practices]] when using this substance. | It is strongly recommended that one use [[harm reduction practices]] when using this substance. | ||
===Lethal dosage=== | ===Lethal dosage=== | ||
The observed LD50 in mice was 100mg/kg via intravenous, 327mg/kg intraperitoneal and > 200mg/kg orally, anasthetic effects were observed at 16mg/kg intraperitoneal.<ref name="OEHA2004">{{cite web | publisher=Office of Environmental Health Hazard Assessment | The observed LD50 in mice was 100mg/kg via intravenous, 327mg/kg intraperitoneal and > 200mg/kg orally, anasthetic effects were observed at 16mg/kg intraperitoneal.<ref name="OEHA2004">{{cite web | publisher=Office of Environmental Health Hazard Assessment California Environmental Protection Agency | title=EVIDENCE ON THE DEVELOPMENTAL AND REPRODUCTIVE TOXICITY OF Progesterone | url=https://oehha.ca.gov/media/downloads/proposition-65/chemicals/progeshid5.pdf | access-date=2024-03-12}}</ref> | ||
California Environmental Protection Agency | title=EVIDENCE ON THE DEVELOPMENTAL AND REPRODUCTIVE TOXICITY OF Progesterone | url=https://oehha.ca.gov/media/downloads/proposition-65/chemicals/progeshid5.pdf | access-date=2024-03-12}}</ref> | |||
===Tolerance and addiction potential=== | ===Tolerance and addiction potential=== | ||
Dependence potential of Progesterone has been sparsely reported by transfeminine people. There is one case report of a women on post menopausal HRT that documents addiction.<ref name="React Weekly 1996 p. 9">{{cite journal | author=&Na; | title=Progesterone abuse Adverse effects: case report | journal=Reactions Weekly | volume=&NA; | issue=599 | date=1996 | issn=0114-9954 | doi=10.2165/00128415-199605990-00031 | page=9}}</ref> | Dependence potential of Progesterone has been sparsely reported by transfeminine people. There is one case report of a women on post menopausal HRT that documents addiction.<ref name="React Weekly 1996 p. 9">{{cite journal | author=&Na; | title=Progesterone abuse Adverse effects: case report | journal=Reactions Weekly | volume=&NA; | issue=599 | date=1996 | issn=0114-9954 | doi=10.2165/00128415-199605990-00031 | page=9}}</ref> | ||
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{{DangerousInteractions/Intro}} | {{DangerousInteractions/Intro}} | ||
*'''[[Depressants]]''' Taking oral progesterone together with [[alcohol]] or [[barbiturates]] will increase absorption rates and peak potentially leading to black out intervals or loss of motor control, anesthetic levels in humans are not documented, but might be reachable. | *'''[[Depressants]]''' Taking oral progesterone together with [[alcohol]] or [[barbiturates]] will increase absorption rates and peak potentially leading to black out intervals or loss of motor control, anesthetic levels in humans are not documented, but might be reachable. | ||
*'''[[Acetylcholine]]''' | *'''[[Acetylcholine]]''' | ||
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==Literature== | ==Literature== | ||
* APA formatted reference | * APA formatted reference | ||
Please see the [[citation formatting guide]] if you need assistance properly formatting citations. | Please see the [[citation formatting guide]] if you need assistance properly formatting citations. | ||