ارژین

ارژین
داده‌های بالینی
نام‌های دیگر	Lysergic acid amide; LSA; LAA; ᴅ-Lysergic acid amide; ᴅ-Lysergamide, d-Lysergamide; LA-111; "Lacy"; 6-Methyl-9,10-didehydroergoline-8β-carboxamide
رده‌بندی داروهای; بارداری	X;
روش مصرف دارو	دهانی, تزریق عضلانی, تزریق زیرجلدی
گروه دارویی	روان‌گردان; توهم‌زا; آرام‌بخش
کد ATC	None;
وضعیت قانونی
وضعیت قانونی	UK: کلاس آ ; US: رده سه ; Illegal in France;
داده‌های فارماکوکینتیک
متابولیسم	Hepatic
اثر دارو	0.3–3 h (morn. glory seeds)
مدت زمان اثر	4–10 h (morn. glory seeds)
دفع	کلیوی
شناسه‌ها
	نام آیوپاک (6aR,9R)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide;
شمارهٔ سی‌ای‌اس	478-94-4 ;
پاب‌کم CID	442072;
کم‌اسپایدر	390611 ;
UNII	073830XH10;
ChEBI	CHEBI:4819 ;
ChEMBL	ChEMBL227213 ;
CompTox Dashboard (EPA)	DTXSID20893673 ;
ECHA InfoCard	100.006.841
داده‌های فیزیکی و شیمیایی
فرمول شیمیایی	C16H17N3O
جرم مولی	۲۶۷٫۳۳۲ g·mol−1
مدل سه بعدی (جی‌مول)	Interactive image;
نقطه ذوب	۱۳۵ درجه سلسیوس (۲۷۵ درجه فارنهایت) Decomposes
	SMILES O=C(N)[C@@H]1C=C2C3=CC=CC4=C3C(C[C@@]2([H])N(C1)C)=CN4;
	InChI InChI=1S/C16H17N3O/c1-19-8-10(16(17)20)5-12-11-3-2-4-13-15(11)9(7-18-13)6-14(12)19/h2-5,7,10,14,18H,6,8H2,1H3,(H2,17,20)/t10-,14-/m1/s1 ; Key:GENAHGKEFJLNJB-QMTHXVAHSA-N ;
	(صحت‌سنجی)

اِرژین (Ergine) که با نام لایزرژیک اسید آمید (به انگلیسی: Lysergic acid amide) یا اِل‌اِس‌اِی (LSA) نیز شناخته می‌شود، یک سایکواکتیو در دسته روان‌گردان‌ها و از آلکالوئیدهای موجود در رز چوبین هاوایی و نیلوفر پیچ است که اثراتی مشابه با ال‌اس‌دی دارد.^[۹]^[۱۲]^[۸]^[۱۳]^[۱۴]

منابع

↑ Oliver JW, Abney LK, Strickland JR, Linnabary RD (October 1993). "Vasoconstriction in bovine vasculature induced by the tall fescue alkaloid lysergamide". Journal of Animal Science. 71 (10): 2708–2713. doi:10.2527/1993.71102708x. PMID 7901191.
↑ Genest K, Sahasrabudhe MR (1966). "Alkaloids and Lipids of Ipomoea, Rivea and Convolvulus and Their Application to Chemotaxonomy". Economic Botany. 20 (4): 416–428. Bibcode:1966EcBot..20..416G. doi:10.1007/BF02904064. ISSN 0013-0001. JSTOR 4252802.
↑ Genest K (November 1966). "Changes in ergoline alkaloids in seeds during ontogeny of Ipomoea violacea". Journal of Pharmaceutical Sciences (in English). 55 (11): 1284–1288. Bibcode:1966JPhmS..55.1284G. doi:10.1002/jps.2600551123. PMID 5969787.
↑ Genest K (September 1965). "A direct densitometric method on thin-layer plates for the determination of lysergic acid amide, isolysergic acid amide and clavine alkaloids in morning glory seeds". Journal of Chromatography. 19 (3): 531–539. doi:10.1016/S0021-9673(01)99495-6. PMID 5864081.
↑ Brown JK, Malone MH (1978-01-01). ""Legal highs"--constituents, activity, toxicology, and herbal folklore". Clinical Toxicology. 12 (1): 1–31. doi:10.3109/15563657809149579. PMID 343978.
↑ "Erowid Morning Glory Basics". Erowid.org. Retrieved 2012-02-03.
↑ "Arrêté du 20 mai 2021 modifiant l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants". www.legifrance.gouv.fr (in French). 20 May 2021.
1 2 3 Tittarelli R, Mannocchi G, Pantano F, Romolo FS (January 2015). "Recreational use, analysis and toxicity of tryptamines". Curr Neuropharmacol. 13 (1): 26–46. doi:10.2174/1570159X13666141210222409. PMC 4462041. PMID 26074742. Ergine, or lysergic acid amide (LSA), is an alkaloid of the ergoline family closely related to LSD, found in the seeds of Argyreia nervosa (Hawaiian baby woodrose) and Ipomoea violacea (Morning Glories). Hallucinogenic activity of LSA occurs with 4-10 seeds of Argyreia nervosa or with 150–200 seeds (3–6 g) of Ipomoea violacea: seeds could be crushed or eaten whole, or also drunk as an extract, after soaking in water [42]. The onset of the hallucinatory effects, after ingestion of Hawaiian Baby Woodrose, is from 20 to 40 minutes and their total duration is from 5 to 8 hours: the plateau is reached after 4-6 hours and the return to normality is after 1-2 hours from the plateau. [...] However, as regards to the assumption of the Morning Glory seeds, the onset of the hallucinatory effects is from 30 to 180 minutes and they last for 4 to 10 hours. The users reported that they return to normality after about 24 hours [67].
1 2 3 Waters K (August 2021). "Pharmacologic Similarities and Differences Among Hallucinogens". J Clin Pharmacol. 61 Suppl 2: S100–S113. doi:10.1002/jcph.1917. PMID 34396556. A study published in 2013 suggests that there may be a resurgence in use [of morning glory seeds] in the United States following its peak in the 1960s, potentially due to the low price, widespread availability, and lack of legal restrictions.45 [...] The mechanism of action of LSA remains unclear; its binding profile has some similarities to that of LSD, but LSA has demonstrated a lower affinity for all receptors.44 Although LSA may produce similar changes in visual perception as elicited by LSD, the psychedelic effects are weaker, likely due to the significantly higher affinity of LSD for 5HT2 receptors.44,45 [...] The seeds of these plants may be ingested whole, ground up, suspended in beverages, or formulated into capsules.11,46 A hallucinogenic dose of LSA ranges from 2 to 5 mg.35 This can generally be obtained from 5 to 10 seeds of Argyreia nervosa (0.14% LSA by dry weight) or 150 to 200 seeds of Ipomoea violacea (0.02% LSA by dry weight).35,47–49 The onset of effects is rapid, and the effects typically last from 4 to 8 hours.35
↑ Paulke A, Kremer C, Wunder C, Toennes SW (August 2012). "Analysis of lysergic acid amide in human serum and urine after ingestion of Argyreia nervosa seeds". Anal Bioanal Chem. 404 (2): 531–538. doi:10.1007/s00216-012-6121-5. PMID 22695498.
↑ خطای یادکرد: خطای یادکرد:برچسب <ref>‎ غیرمجاز؛ متنی برای یادکردهای با نام SmithTimmis1932 وارد نشده است. (صفحهٔ راهنما را مطالعه کنید.).
↑ Steiner U, Leistner E (July 2018). "Ergot Alkaloids and their Hallucinogenic Potential in Morning Glories" (PDF). Planta Med. 84 (11): 751–758. Bibcode:2018PlMed..84..751S. doi:10.1055/a-0577-8049. PMID 29499587.
↑ Grof S, Hofmann A (Fall 2001) [1984]. "Stanislav Grof Interviews Dr. Albert Hofmann". MAPS Bulletin. 9 (2): 22–35.
↑ خطای لوآ در پودمان:Citation/CS1/en/Identifiers در خط 156: attempt to compare two nil values.

مشارکت‌کنندگان ویکی‌پدیا. «Ergine». در دانشنامهٔ ویکی‌پدیای انگلیسی.

[OliverAbneyStrickland1993-1] Oliver JW, Abney LK, Strickland JR, Linnabary RD (October 1993). "Vasoconstriction in bovine vasculature induced by the tall fescue alkaloid lysergamide". Journal of Animal Science. 71 (10): 2708–2713. doi:10.2527/1993.71102708x. PMID 7901191.

[GenestSahasrabudhe1966-2] Genest K, Sahasrabudhe MR (1966). "Alkaloids and Lipids of Ipomoea, Rivea and Convolvulus and Their Application to Chemotaxonomy". Economic Botany. 20 (4): 416–428. Bibcode:1966EcBot..20..416G. doi:10.1007/BF02904064. ISSN 0013-0001. JSTOR 4252802.

[Genest1966-3] Genest K (November 1966). "Changes in ergoline alkaloids in seeds during ontogeny of Ipomoea violacea". Journal of Pharmaceutical Sciences (in English). 55 (11): 1284–1288. Bibcode:1966JPhmS..55.1284G. doi:10.1002/jps.2600551123. PMID 5969787.

[Genest1965-4] Genest K (September 1965). "A direct densitometric method on thin-layer plates for the determination of lysergic acid amide, isolysergic acid amide and clavine alkaloids in morning glory seeds". Journal of Chromatography. 19 (3): 531–539. doi:10.1016/S0021-9673(01)99495-6. PMID 5864081.

[BrownMalone1978-5] Brown JK, Malone MH (1978-01-01). ""Legal highs"--constituents, activity, toxicology, and herbal folklore". Clinical Toxicology. 12 (1): 1–31. doi:10.3109/15563657809149579. PMID 343978.

[Erowid-Morning-Glory-6] "Erowid Morning Glory Basics". Erowid.org. Retrieved 2012-02-03.

[LegiFrance2021-7] "Arrêté du 20 mai 2021 modifiant l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants". www.legifrance.gouv.fr (in French). 20 May 2021.

[TittarelliMannocchiPantano2015-8] 1 2 3 Tittarelli R, Mannocchi G, Pantano F, Romolo FS (January 2015). "Recreational use, analysis and toxicity of tryptamines". Curr Neuropharmacol. 13 (1): 26–46. doi:10.2174/1570159X13666141210222409. PMC 4462041. PMID 26074742. Ergine, or lysergic acid amide (LSA), is an alkaloid of the ergoline family closely related to LSD, found in the seeds of Argyreia nervosa (Hawaiian baby woodrose) and Ipomoea violacea (Morning Glories). Hallucinogenic activity of LSA occurs with 4-10 seeds of Argyreia nervosa or with 150–200 seeds (3–6 g) of Ipomoea violacea: seeds could be crushed or eaten whole, or also drunk as an extract, after soaking in water [42]. The onset of the hallucinatory effects, after ingestion of Hawaiian Baby Woodrose, is from 20 to 40 minutes and their total duration is from 5 to 8 hours: the plateau is reached after 4-6 hours and the return to normality is after 1-2 hours from the plateau. [...] However, as regards to the assumption of the Morning Glory seeds, the onset of the hallucinatory effects is from 30 to 180 minutes and they last for 4 to 10 hours. The users reported that they return to normality after about 24 hours [67].

[Waters2021-9] 1 2 3 Waters K (August 2021). "Pharmacologic Similarities and Differences Among Hallucinogens". J Clin Pharmacol. 61 Suppl 2: S100–S113. doi:10.1002/jcph.1917. PMID 34396556. A study published in 2013 suggests that there may be a resurgence in use [of morning glory seeds] in the United States following its peak in the 1960s, potentially due to the low price, widespread availability, and lack of legal restrictions.45 [...] The mechanism of action of LSA remains unclear; its binding profile has some similarities to that of LSD, but LSA has demonstrated a lower affinity for all receptors.44 Although LSA may produce similar changes in visual perception as elicited by LSD, the psychedelic effects are weaker, likely due to the significantly higher affinity of LSD for 5HT2 receptors.44,45 [...] The seeds of these plants may be ingested whole, ground up, suspended in beverages, or formulated into capsules.11,46 A hallucinogenic dose of LSA ranges from 2 to 5 mg.35 This can generally be obtained from 5 to 10 seeds of Argyreia nervosa (0.14% LSA by dry weight) or 150 to 200 seeds of Ipomoea violacea (0.02% LSA by dry weight).35,47–49 The onset of effects is rapid, and the effects typically last from 4 to 8 hours.35

[PaulkeKremerWunder2012-10] Paulke A, Kremer C, Wunder C, Toennes SW (August 2012). "Analysis of lysergic acid amide in human serum and urine after ingestion of Argyreia nervosa seeds". Anal Bioanal Chem. 404 (2): 531–538. doi:10.1007/s00216-012-6121-5. PMID 22695498.

[SmithTimmis1932-11] خطای یادکرد: خطای یادکرد:برچسب <ref>‎ غیرمجاز؛ متنی برای یادکردهای با نام SmithTimmis1932 وارد نشده است. (صفحهٔ راهنما را مطالعه کنید.).

[SteinerLeistner2018-12] Steiner U, Leistner E (July 2018). "Ergot Alkaloids and their Hallucinogenic Potential in Morning Glories" (PDF). Planta Med. 84 (11): 751–758. Bibcode:2018PlMed..84..751S. doi:10.1055/a-0577-8049. PMID 29499587.

[GrofHofmann1984-13] Grof S, Hofmann A (Fall 2001) [1984]. "Stanislav Grof Interviews Dr. Albert Hofmann". MAPS Bulletin. 9 (2): 22–35.

[HazelPanaccione2025-14] خطای لوآ در پودمان:Citation/CS1/en/Identifiers در خط 156: attempt to compare two nil values.

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