麥角酸二乙酰胺:修订间差异

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{{Infobox drug

{{Chembox
| Name = D-麦角酸二乙胺
| Verifiedfields = changed
| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 420331797
| verifiedrevid = 629704081
| IUPAC_name = (6a''R'',9''R'')-''N'',''N''-diethyl-7-methyl-4,6,6a,7,8,9-hexahydroindolo-[4,3-''fg'']quinoline-9-carboxamide
| ImageFile = LSD-2D-skeletal-formula-and-3D-models.png
| image = LSD-2D-skeletal-formula-and-3D-models.png
| ImageSize = 300px

| ImageName =
<!--Clinical data-->
| IUPACName = (6a''R'',9''R'')-''N'',''N''-diethyl<br />-7-methyl-4,6,6a,7,8,9-<br />
| pregnancy_US = C
hexahydroindolo-[4,3-''fg'']<br />quinoline-9-carboxamide
| legal_AU = Schedule 9
| IUPACNameZh =
| legal_CA = Schedule III
| OtherNames = LSD, LSD-25,<br /> lysergide, <br /><small>D</small>-lysergic acid diethyl amide, <br /> ''N'',''N''- diethyl- <small>D</small>- lysergamide
| legal_NZ = Class A
| Section1 = {{Chembox Identifiers
| CASNo = 50-37-3
| legal_UK = Class A
| legal_UN = P I
| CASNo_Ref = {{cascite|correct|CAS}}
| legal_US = Schedule I
| legal_DE = Anlage I
| addiction_liability = 无<ref name="NHM-MDMA">{{cite book | author = Malenka RC, Nestler EJ, Hyman SE | editor = Sydor A, Brown RY | title = Molecular Neuropharmacology: A Foundation for Clinical Neuroscience | year = 2009 | publisher = McGraw-Hill Medical | location = New York | isbn = 9780071481274 | page = 375 | edition = 2nd | chapter = Chapter 15: Reinforcement and Addictive Disorders | quote= Several other classes of drugs are categorized as drugs of abuse but rarely produce compulsive use. These include psychedelic agents, such as lysergic acid diethylamide (LSD), which are used for their ability to produce perceptual distortions at low and moderate doses. The use of these drugs is associated with the rapid development of tolerance and the absence of positive reinforcement (Chapter 6). Partial agonist effects at 5HT2A receptors are implicated in the psychedelic actions of LSD and related hallucinogens. 3,4-Methylenedioxymethamphetamine (MDMA), commonly called ecstasy, is an amphetamine derivative. It produces a combination of psychostimulant-like and weak LSD-like effects at low doses. Unlike LSD, MDMA is reinforcing—most likely because of its interactions with dopamine systems—and accordingly is subject to compulsive abuse. The weak psychedelic effects of MDMA appear to result from its amphetamine-like actions on the serotonin reuptake transporter, by means of which it causes transporter-dependent serotonin efflux. MDMA has been proven to produce lesions of serotonin neurons in animals and humans.}}</ref>
| dependency_liability = Low<ref>{{cite book|last1=Halpern|first1=John H.|last2=Suzuki|first2=Joji|last3=Huertas,|first3=Pedro E.|last4=Passie|first4=Torsten|editor1-last=Price|editor1-first=Lawrence H.|editor2-last=Stolerman|editor2-first=Ian P.|title=Encyclopedia of Psychopharmacology A Springer Live Reference|date=7 June 2014|publisher=Springer-Verlag Berlin Heidelberg|location=Heidelberg, Germany|isbn=978-3-642-27772-6|pages=1-5|url=http://link.springer.com/referenceworkentry/10.1007/978-3-642-27772-6_43-2|accessdate=24 April 2015|quote=Hallucinogen abuse and dependence are known complications resulting from the illicit use of drugs in this category, such as LSD and psilocybin. Users do not experience withdrawal symptoms, but the general criteria for substance abuse and dependence otherwise apply. Dependence is estimated in approximately 2 % of recent-onset users in the United States.}}</ref>
| routes_of_administration = [[口服]], [[舌下]], [[静注]], [[眼睑]], [[肌注]]

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| elimination_half-life = 3–5 小时<ref name="Aghajanian" /><ref name="Papac" />
| excretion = [[Renal]]

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| InChI = 1S/C20H25N3O/c1-4-23(5-2)20(24)14-9-16-15-7-6-8-17-19(15)13(11-21-17)10-18(16)22(3)12-14/h6-9,11,14,18,21H,4-5,10,12H2,1-3H3/t14-,18-/m1/s1
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| C=20 | H=25 | N=3 | O=1
| smiles = CCN(CC)C(=O)[C@H]1CN([C@@H]2Cc3c[nH]c4c3c(ccc4)C2=C1)C
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| synonyms = Acid, LSD, lysergide
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| C=20 | H=25 | N=3 | O=1
| Formula =
| MolarMass = 323.43 g/mol
| MolarMass_notes =
| ExactMass =
| MolarMassOther =
| Appearance = 無色、無氣味,无味道(纯LSD味微苦)
| Density = 1.21g/cm<sup>3</sup>
| MeltingPt = 80-85 ºC
| BoilingPt = 541.3 ºC<ref>[http://www.guidechem.com/cas-50/50-37-3.html LSD] guidechem.com [2013-12-14]</ref>
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| Section4 = {{Chembox Pharmacology
| Reference =
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| AdminRoutes =
| Metabolism = [[肝臟]]
| Metabolites =
| HalfLife = 3–5 [[小時]]<ref name="Aghajanian">
{{cite journal
|last1=Aghajanian
|first1=George K.
|last2=Bing
|first2=Oscar H. L.
|title=Persistence of lysergic acid diethylamide in the plasma of human subjects
|year=1964
|journal=Clinical Pharmacology and Therapeutics
|volume=5
|pages=611–614
|url=http://www.maps.org/w3pb/new/1964/1964_aghajanian_2224_1.pdf
|format=PDF
|accessdate=2009-09-17
|pmid=14209776}}</ref><ref name="Papac">
{{cite journal
|last1=Papac
|first1=DI
|last2=Foltz
|first2=RL
|title=Measurement of lysergic acid diethylamide (LSD) in human plasma by gas chromatography/negative ion chemical ionization mass spectrometry
|year=1990
|month=May/June
|journal=Journal of Analytical Toxicology
|volume=14
|issue=3
|pages=189–190
|url=http://www.erowid.org/references/refs_view.php?A=ShowDocPartFrame&C=ref&ID=6265&DocPartID=6624
|format=PDF
|accessdate=2009-09-17
|pmid=2374410}}</ref>
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| Legal_CA = Schedule III
| Legal_UK = CD
| Legal_US = Schedule I
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| PregCat_CA =
| PregCat_DE =
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| Section5 = {{NewLine|{{Chembox header}}|治療考量|table2|{{NewLine|[[懷孕分級]]|C <sub>([[美國|美]])</sub>|table}}<nowiki></nowiki>{{NewLine|[[治療產品管理|合法狀態]]|[[藥物和毒物標準統一目錄|違禁藥物 (S9)]] <sub>([[澳大利亞|澳]])</sub> [[加拿大管制藥品及藥物法|附錄三]] <sub>([[加拿大|加]])</sub> CD ([[英國|英]]) [[美國管製藥品法|附錄一]] <sub>([[美國|美]])</sub>|table}}<nowiki></nowiki>{{NewLine|[[給藥途徑|途徑]]|[[口腔|口服]], [[靜脈注射]], [[人眼|眼部]], [[肌肉注射]]|table}}<nowiki></nowiki>{{NewLine|[[物質依賴|依賴傾向]]|Very low|table}}}}
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}}
D-'''麥角酸二乙胺'''(Lysergic acid diethylamide),也称为“'''麦角二乙酰胺'''”,常简称为“'''LSD'''”,是一种强烈的半人工[[致幻劑]]。它由[[麥角酸]]中合成,對[[氧氣]]、[[紫外線]]與[[氯]]十分敏感(尤其是当LSD处于[[液態]]時)。纯净的LSD是一种無色、無氣味,味微苦的固体<ref>{{cite book |title= [[PiHKAL]] |publisher= Transform Press |author1= Shulgin, Alexander |author2= Shulgin, Ann |year=1991 |edition=1st |chapter=Burt |page=21 |isbn= 978-0-9630096-0-9}}</ref>。LSD的一次典型[[劑量]]只有100[[μg|微克]],仅相當於一粒沙子重量的十分之一,能造成使用者6到12[[小時]]的[[感官]]、[[感覺]]、[[記憶]]和[[自我意識]]的強烈化與變化,可作化學武器使用。LSD一般[[口服]],通常以某種吸取物質吸取LSD后再服用该物(比如用吸墨紙、方糖或[[明膠]]吸取LSD後再將該吸取物放入口中),不過也可以通過[[食物]]或[[飲料]]來服用。在英國、美國、澳洲、新西蘭和大部分歐洲國家,這藥物都是非法的。
D-'''麥角酸二乙胺'''(Lysergic acid diethylamide),也称为“'''麦角二乙酰胺'''”,常简称为“'''LSD'''”,是一种强烈的半人工[[致幻劑]]。它由[[麥角酸]]中合成,對[[氧氣]]、[[紫外線]]與[[氯]]十分敏感(尤其是当LSD处于[[液態]]時)。纯净的LSD是一种無色、無氣味,味微苦的固体<ref>{{cite book |title= [[PiHKAL]] |publisher= Transform Press |author1= Shulgin, Alexander |author2= Shulgin, Ann |year=1991 |edition=1st |chapter=Burt |page=21 |isbn= 978-0-9630096-0-9}}</ref>。LSD的一次典型[[劑量]]只有100[[μg|微克]],仅相當於一粒沙子重量的十分之一,能造成使用者6到12[[小時]]的[[感官]]、[[感覺]]、[[記憶]]和[[自我意識]]的強烈化與變化,可作化學武器使用。LSD一般[[口服]],通常以某種吸取物質吸取LSD后再服用该物(比如用吸墨紙、方糖或[[明膠]]吸取LSD後再將該吸取物放入口中),不過也可以通過[[食物]]或[[飲料]]來服用。在英國、美國、澳洲、新西蘭和大部分歐洲國家,這藥物都是非法的。

2015年10月14日 (三) 13:38的版本

麥角酸二乙酰胺
臨床資料
其他名稱Acid, LSD, lysergide
依賴性Low[1]
成癮性[2]
给药途径口服, 舌下, 静注, 眼睑, 肌注
ATC碼
  • 未分配
法律規範狀態
法律規範
藥物動力學數據
药物代谢肝脏
生物半衰期3–5 小时[3][4]
排泄途徑Renal
识别信息
  • (6aR,9R)-N,N-diethyl-7-methyl-4,6,6a,7,8,9-hexahydroindolo-[4,3-fg]quinoline-9-carboxamide
CAS号50-37-3  checkY
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard英语CompTox Chemicals Dashboard (EPA)
ECHA InfoCard100.000.031 編輯維基數據鏈接
化学信息
化学式C20H25N3O
摩尔质量323.44 g·mol−1
3D模型(JSmol英语JSmol
熔点80至85 °C(176至185 °F)
  • CCN(CC)C(=O)[C@H]1CN([C@@H]2Cc3c[nH]c4c3c(ccc4)C2=C1)C
  • InChI=1S/C20H25N3O/c1-4-23(5-2)20(24)14-9-16-15-7-6-8-17-19(15)13(11-21-17)10-18(16)22(3)12-14/h6-9,11,14,18,21H,4-5,10,12H2,1-3H3/t14-,18-/m1/s1 checkY
  • Key:VAYOSLLFUXYJDT-RDTXWAMCSA-N checkY

D-麥角酸二乙胺(Lysergic acid diethylamide),也称为“麦角二乙酰胺”,常简称为“LSD”,是一种强烈的半人工致幻劑。它由麥角酸中合成,對氧氣紫外線十分敏感(尤其是当LSD处于液態時)。纯净的LSD是一种無色、無氣味,味微苦的固体[5]。LSD的一次典型劑量只有100微克,仅相當於一粒沙子重量的十分之一,能造成使用者6到12小時感官感覺記憶自我意識的強烈化與變化,可作化學武器使用。LSD一般口服,通常以某種吸取物質吸取LSD后再服用该物(比如用吸墨紙、方糖或明膠吸取LSD後再將該吸取物放入口中),不過也可以通過食物飲料來服用。在英國、美國、澳洲、新西蘭和大部分歐洲國家,這藥物都是非法的。

歷史

“LSD”是德文Lysergsäure-diäthylamid)的簡寫。它在1938年巴塞爾桑多茲實驗室(Sandoz Laboratories)由瑞士化學家艾伯特·霍夫曼博士,於進行一個有關麥角鹼類複合物的大型研究計畫時第一次被合成出來。1943年,霍夫曼在一次意外的接觸中透過皮膚吸收了微量的LSD,從而發現LSD的精神轉換效果,促使他繼續在他自己身上試驗LSD[6]

直到1966年,桑多茲實驗室仍提供免費的LSD和光盖伞素給有興趣研究的科學家,使精神病學家也可使用這些化合物來使自己得到對精神分裂症的親身體驗。許多臨床實驗中,把LSD使用於精神治療的可能性都得到非常正面的結果。{cn}

LSD在1950年代首度大眾娛樂化,流行於一小群心理健康專家(比如精神病學家和心理學家)和一些政治和社會上的重要人士之間(如亨利·路斯)。

冷戰時期的情報部門曾將LSD用在審問心理控制上(如MKUltra計劃),以及在大規模的社交工程(請見反文化)上。美國中央情報局對LSD進行了廣泛的研究,但當中絕大部分都被銷毀。

一些心理健康專家,如哈佛大學心理學教授提莫西·李瑞博士和理察·艾爾帕博士(後來以拉姆·達斯聞名),相信LSD具作為精神成長工具的潛力。这些心理健康專家被傳統心理學術圈排斥,並且在1960年代的嬉皮士運動中成為反文化的精神導師,將LSD的使用擴展到更廣大的群眾。當LSD與反文化和嬉皮的關係變得越來越密切時,它在1967年被美國政府禁止。

在1990年代,LSD於锐舞次文化中受到歡迎。在美國藥品管制局有史以來最大一宗的LSD查緝案後,美國LSD的使用大約在2000年急劇下滑。美國藥品管制局逮捕了兩名化學家,並聲稱他們製造了美國與許多歐洲地區LSD供應量中95%的LSD。

从1967年开始,在黑市和大量需求的支持下,LSD的地下娱乐性和治疗性使用开始在一些国家继续。对LSD的效果和作用机制的合法的科学实验也不时进行,但很少涉及人类主体。

潛在用途

LSD有药用价值,有时候用于治疗酒精上瘾、缓解疼痛、集束性头痛,也有用作提升创造力。但是如美国禁毒署之类的政府组织坚称「LSD没有兴奋刺激作用,不能提升创造力,对酒精依赖没有持续的积极的疗效,不会产生典型的精神错乱,也不会产生立即的人格改变」。

精神治療

從1950年代到1960年代,LSD被用于增强精神病治疗的疗效。有些精神病专家认为LSD对于帮助病人通过其他精神治疗手段「解开」受压抑的潜意识内容和治疗酒精上瘾十分有效。 一项研究指出,「LSD药用价值的根本即它有产生自我接受和自我降服的潜力,」可能是强迫使用者面对精神问题。在1968年12月,一份由74位英国医生發起的调查反映了LSD的临床效果。在73份回复中,大多数医生认为LSD效果明显且足够安全。

  1. 56%即41人继续在临床使用LSD。
  2. 15%即11人停止使用因为退休或是其他客观原因。
  3. 12%即9人停止使用LSD因为它们发现药效不明显。
  4. 10%即7人停止使用且原因不明。
  5. 7%即5人停止使用因为LSD过于危险。

劑量

LSD按质量而言是迄今为止发现的最强烈的精神药品之一。从试验者的体验和药物学方法(例如受体结合实验)中,都发现LSD比光盖伞素光盖伞辛要强100倍,比墨斯卡林强4000倍。LSD的剂量以微克为单位,相对而言几乎所有其他的药品毒品都以毫克为单位。

通常LSD的致幻剂量为25μg,且其药效随剂量增加而显著加强。1990年代末,美国缉毒警察缴获的LSD每支大约20-80μg;60年代时也有300μg以上的。常用LSD的人的可达剂量为1200μg,但是如此高的剂量可能会产生不愉快的生理心理反应。

LSD的致死剂量(LD50)为200-1000μg/kg,但迄今为止尚未有LSD过量致死的报道。有一个可疑LSD过量致死的报道,死者用静脉注射的方法使用了三分之一克的LSD(即330mg,330,000μg),这相当于3000倍的通常口服剂量。

藥效

生理

  • 是迷幻性最強的藥。從圖中可見,LSD對身體造成的生理傷害和依賴性與搖頭丸等毒品相當,但遠不如香煙酒精來的嚴重。
縱軸是成癮性、橫軸是傷害性。資料來自權威醫學期刊:The Lancet
  • 服用可能導致逼真幻覺、時空幻覺。
  • 長期服用可能有旅行片段(英文俗称“acid trip”)。

心理

具成瘾性,可能会产生心理依赖。

另見

参考文献

  1. ^ Halpern, John H.; Suzuki, Joji; Huertas,, Pedro E.; Passie, Torsten. Price, Lawrence H.; Stolerman, Ian P. , 编. Encyclopedia of Psychopharmacology A Springer Live Reference. Heidelberg, Germany: Springer-Verlag Berlin Heidelberg. 7 June 2014: 1–5 [24 April 2015]. ISBN 978-3-642-27772-6. Hallucinogen abuse and dependence are known complications resulting from the illicit use of drugs in this category, such as LSD and psilocybin. Users do not experience withdrawal symptoms, but the general criteria for substance abuse and dependence otherwise apply. Dependence is estimated in approximately 2 % of recent-onset users in the United States. 
  2. ^ Malenka RC, Nestler EJ, Hyman SE. Chapter 15: Reinforcement and Addictive Disorders. Sydor A, Brown RY (编). Molecular Neuropharmacology: A Foundation for Clinical Neuroscience 2nd. New York: McGraw-Hill Medical. 2009: 375. ISBN 9780071481274. Several other classes of drugs are categorized as drugs of abuse but rarely produce compulsive use. These include psychedelic agents, such as lysergic acid diethylamide (LSD), which are used for their ability to produce perceptual distortions at low and moderate doses. The use of these drugs is associated with the rapid development of tolerance and the absence of positive reinforcement (Chapter 6). Partial agonist effects at 5HT2A receptors are implicated in the psychedelic actions of LSD and related hallucinogens. 3,4-Methylenedioxymethamphetamine (MDMA), commonly called ecstasy, is an amphetamine derivative. It produces a combination of psychostimulant-like and weak LSD-like effects at low doses. Unlike LSD, MDMA is reinforcing—most likely because of its interactions with dopamine systems—and accordingly is subject to compulsive abuse. The weak psychedelic effects of MDMA appear to result from its amphetamine-like actions on the serotonin reuptake transporter, by means of which it causes transporter-dependent serotonin efflux. MDMA has been proven to produce lesions of serotonin neurons in animals and humans. 
  3. ^ 引用错误:没有为名为Aghajanian的参考文献提供内容
  4. ^ 引用错误:没有为名为Papac的参考文献提供内容
  5. ^ Shulgin, Alexander; Shulgin, Ann. Burt. PiHKAL 1st. Transform Press. 1991: 21. ISBN 978-0-9630096-0-9. 
  6. ^ 完整故事

外部連結

媒體

提莫西·李瑞

學術

都市傳奇

其他