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LSD

Clinical data
Other names	LSD, LSD-25, lysergide, d-lysergic acid diethylamide, N,N-diethyl-d-lysergamide
Pregnancy category	AU: X (High risk)
Routes of administration	Oral, Intravenous, Transdermal
Legal status
Legal status	AU: S9 (Prohibited substance) CA: Schedule IV UK: Class A US: Schedule I
Pharmacokinetic data
Metabolism	hepatic
Elimination half-life	3 hours
Excretion	renal
Identifiers
IUPAC name (6aR,9R)-N,N-diethyl-7-methyl-4,6,6a,7,8,9- hexahydroindolo-quinoline-9-carboxamide
CAS Number	50-37-3
PubChem CID	5761
CompTox Dashboard (EPA)	DTXSID1023231
ECHA InfoCard	100.000.031
Chemical and physical data
Formula	C20H25N3O
Molar mass	323.43 g/mol g·mol
3D model (JSmol)	Interactive image
Melting point	80 °C (176 °F)
SMILES CN1(C2=C (C(N(CC)CC)=O)C1)() CC3=CNC4=C3C2=CC=C4

Lysergic acid diethylamide, commonly called LSD, LSD-25, or acid, is a semisynthetic psychedelic drug, synthesized from lysergic acid derived from ergot, a grain fungus that typically grows on rye. The short form LSD comes from the German LSDM, "Lyserg säure-diethylamid".

LSD is sensitive to oxygen, ultraviolet light, and chlorine, especially in solution (though its potency may last years if it is stored away from light and moisture at low temperature). In pure form it is colorless, odorless and mildly bitter. LSD is typically delivered orally, usually on a substrate such as absorbent blotter paper, a sugar cube, or gelatin. In its liquid form, it can be administered by intramuscular or intravenous injection, or even in the form of eye-drops. In its blotter paper form, it is popularly taken by placing a "tab" in the user's mouth for several minutes. The threshold dosage level for an effect on humans is of the order of 20 to 30 micrograms.

Introduced by Sandoz Laboratories as a drug with various psychiatric uses, LSD quickly became a therapeutic agent that appeared to show great promise. However, the extra-medical use of the drug in Western society in the middle years of the twentieth century led to a political firestorm that resulted in the banning of the substance for medical as well as recreational and spiritual uses. Despite this, it is still considered a promising drug in some intellectual circles, and organizations such as MAPS, Heffter Research Institute and the Albert Hofmann Foundation exist to fund, encourage and coordinate research into its medical uses.

Swiss chemist Dr. Albert Hofmann at the Sandoz Laboratories in Basel, Switzerland, as part of a large research program

Pahnke conducted the Good Friday Marsh Chapel Experiment under Leary's supervision, performing a double blind experiment on the administration of psilocybin to volunteers who were students in religious graduate programs, e.g., divinity or theology. That study provided

Chemistry

LSD is an example of an ergoline derivative. It is commonly produced from lysergic acid, which is made from ergotamine, a substance derived from the ergot fungus on rye, or from ergine (lysergic acid amide). LSA, lysergic acid amide, is the sister chemical of LSD found in morning glory and hawaiian baby woodrose seeds. It is theoretically possible to manufacture LSD from morning glory or hawaiian baby woodrose seed. LSD is a chiral compound with two stereocenters at the carbon atoms C-5 and C-8, so that theoretically four different optical isomers of LSD could exist. LSD, also called (+)-D-LSD, has the absolute configuration (5R,8R). The C-5 isomers of lysergamides do not exist in nature and are not formed during the synthesis from D-lysergic acid. However, LSD and iso-LSD, the two C-8 isomers, rapidly interconvert in the presence of base. Non-psychoactive iso-LSD which has formed during the synthesis can be removed by chromatography and can be isomerized to LSD.

Stability

"LSD," writes the chemist Alexander Shulgin, "is an unusually fragile molecule." It is stable for indefinite amounts of time if stored, as a salt or in water, at low temperature and protected from air and light exposure. Two portions of its molecular structure are particularly sensitive, the carboxamide attachment at the 8-position and the double bond between the 8-position and the aromatic ring. The former is affected by high pH, and if perturbed will produce isolysergic acid diethylamide (iso-LSD), which is biologically inactive. If water or alcohol adds to the double bond (especially in the presence of light), LSD converts to "lumi-LSD", which is totally inactive in human beings, to the best of current knowledge. Furthermore, chlorine destroys LSD molecules on contact; even though chlorinated tap water typically contains only a slight amount of chlorine, because a typical LSD solution only contains a small amount of LSD, dissolving LSD in tap water is likely to completely eliminate the substance.

A controlled study was undertaken to determine the stability of LSD in pooled urine samples. The concentrations of LSD in urine samples were followed over time at various temperatures, in different types of storage containers, at various exposures to different wavelengths of light, and at varying pH values. These studies demonstrated no significant loss in LSD concentration at 25 degrees C for up to 4 weeks. After 4 weeks of incubation, a 30% loss in LSD concentration at 37 degrees C and up to a 40% at 45 degrees C were observed. Urine fortified with LSD and stored in amber glass or nontransparent polyethylene containers showed no change in concentration under any light conditions. Stability of LSD in transparent containers under light was dependent on the distance between the light source and the samples, the wavelength of light, exposure time, and the intensity of light. After prolonged exposure to heat in alkaline pH conditions, 10 to 15% of the parent LSD epimerized to iso-LSD. Under acidic conditions, less than 5% of the LSD was converted to iso-LSD. It was also demonstrated that trace amounts of metal ions in buffer or urine could catalyze the decomposition of LSD and that this process can be avoided by the addition of EDTA.

Production

Because an active dose of LSD is astonishingly minute, a large number of doses can be synthesized from a comparatively small amount of raw material. Beginning with ergotamine tartrate, for example, one can manufacture roughly one kilogram of pure, crystalline LSD from five kilograms of tartrate. Five kilograms of LSD — 25 kilograms of ergotamine tartrate — could provide 100 million "hits", sufficient for supplying the entire illicit demand of the United States. Since the masses involved are so small, concealing and transporting illicit LSD is much easier than smuggling other illegal drugs (say, cocaine or cannabis) in equal dosage quantities.

Manufacturing LSD requires laboratory equipment and experience in the field of organic chemistry. It takes two or three days to produce 30 to 100 grams of pure compound. It is believed that LSD usually is not produced in large quantities, but rather in a series of small batches. This technique minimizes the loss of precursor chemicals in case a synthesis step does not work as expected.

Forms of LSD

LSD is produced in crystalline form and then mixed with excipients or redissolved for production in ingestible forms. Liquid solution is either distributed as-is in small vials or, more commonly, sprayed onto or soaked into a distribution medium. Historically, LSD solutions were first sold on sugar cubes, but practical considerations forced a change to tablet form. Early pills or tabs were flattened on both ends and identified by color: "grey flat", "blue flat", and so forth. Next came "domes", which were rounded on one end, then "double domes" rounded on both ends, and finally small tablets known as "microdots". Later still, LSD began to be distributed in thin squares of gelatin ("window panes", "gel tabs") and, most commonly, as blotter paper: sheets of paper impregnated with LSD and perforated into small squares of individual dosage units. The paper is then cut into small square pieces called "tabs" or "hits" for distribution. Individual producers often print designs onto the paper serving to identify different makers, batches or strengths, and such "blotter art" often emphasizes psychedelic themes.

LSD has been sold under a wide variety of street names including Acid, Trips, Alice Dee, 'Cid/Sid, Barrels, Blotter, Doses, Fry, "L", Liquid, Liquid A, Lucy, Lucy in the Sky with Diamonds, Microdots, Mind detergent, Orange cubes, Orange micro, Owsley, Hits, Paper acid, Sacrament, Sandoz, Sugar, Sugar lumps, Sunshine, Tabs, Ticket, Twenty-five, Wedding bells, Windowpane, etc., as well as names that reflect the designs on the sheets of blotter paper. On occasion, authorities have encountered the drug in other forms — including powder or crystal, and capsule. More than 200 types of LSD tablets have been encountered since 1969 and more than 350 paper designs have been observed since 1975. Designs range from simple five-point stars in black and white to exotic artwork in full four-color print.

Legal status

The United Nations Convention on Psychotropic Substances (adopted in 1971) requires its parties to prohibit LSD. Hence, it is illegal in all parties to the convention, which includes the United States, Australia, and most of Europe. However, enforcement of extant laws varies from country to country.

LSD is easy to conceal and smuggle. A tiny vial can contain thousands of doses. Not much money is made from retail-level sales of LSD, so the drug is typically not associated with the violent organized criminal organizations involved in cocaine and opiate smuggling.

Canada

In Canada, LSD is a controlled substance under Schedule III of the Controlled Drugs and Substances Act (CDSA). Every person who seeks to obtain the substance without disclosing authorization to obtain such substances 30 days prior to obtaining another prescription from a practitioner is guilty of an indictable offence and liable to imprisonment for a term not exceeding 3 years. Possession for purpose of trafficking is guilty of an indictable offence and liable to imprisonment for 10 years.

Hong Kong

In Hong Kong, Lysergide and derivatives are regulated under Schedule 1 of Hong Kong's Chapter 134 Dangerous Drugs Ordinance, and can only be used legally by health professionals and for university research purposes. The substance can be given by pharmacists under a prescription. Anyone who supplies the substance without presciption can be fined $10000(HKD). The penalty for trafficking or illegally manufacturing the substance is a $5,000,000 (HKD) fine and life imprisonment. Possession of the substance for consumption without license from the Department of Health is illegal with a $1,000,000 (HKD) fine and/or 7 years' imprisonment.

United States: Prior to 1967

Beginning in the 1950's the Central Intelligence Agency began a research program code named Project MKULTRA. Experiments included administering LSD to CIA employees, military personnel, doctors, other government agents, prostitutes, mentally ill patients, and members of the general public in order to study their reactions, usually without the subject's knowledge. The project was revealed in the US congressional Rockefeller Commission report.

Prior to October 6th, 1966, LSD was available legally in the United States as an experimental psychiatric drug. (LSD "apostle" Al Hubbard actively promoted the drug between the 1950s and the 1970s and introduced thousands of people to it.) The US Federal Government classified it as a Schedule I drug according to the Controlled Substances Act of 1970. As such, the Drug Enforcement Administration holds that LSD meets the following three criteria: it is deemed to have a high potential for abuse; it has no legitimate medical use in treatment; and there is a lack of accepted safety for its use under medical supervision. (LSD prohibition does not make an exception for religious use.) Lysergic acid and lysergic acid amide, LSD precursors, are both classified in Schedule III of the Controlled Substances Act. Ergotamine tartrate, a precursor to lysergic acid, is regulated under the Chemical Diversion and Trafficking Act.

LSD has been manufactured illegally since the 1960s. Historically, LSD was distributed not for profit, but because those who made and distributed it truly believed that the psychedelic experience could do good for humanity, that it expanded the mind and could bring understanding and love. A limited number of chemists, probably fewer than a dozen, are believed to have manufactured nearly all of the illicit LSD available in the United States. The best known of these is undoubtedly Augustus Owsley Stanley III, usually known simply as Owsley. The former chemistry student set up a private LSD lab in the mid-Sixties in San Francisco and supplied the LSD consumed at the famous Merry Pranksters parties held by Ken Kesey and his Merry Pranksters, and other major events such as the Gathering of the tribes in San Francisco in January 1967. He also had close social connections to leading San Francisco bands the Grateful Dead, Jefferson Airplane and Big Brother and The Holding Company, regularly supplied them with his LSD and also worked as their live sound engineer and made many tapes of these groups in concert. Owsley's LSD activities — immortalized by Steely Dan in their song "Kid Charlemagne" — ended with his arrest at the end of 1967, but some other manufacturers probably operated continuously for 30 years or more. Announcing Owsley's first bust in 1966, The San Francisco Chronicle's headline "LSD Millionaire Arrested" inspired the rare Grateful Dead song "Alice D. Millionaire."

United States: 1970 to the present

American LSD usage declined in the 1970s and 1980s, then experienced a mild resurgence in popularity in the 1990s. Although there were many distribution channels during this decade, the U.S. DEA identified continued tours by the psychedelic rock band The Grateful Dead and the then-burgeoning rave scene as primary venues for LSD trafficking and consumption. American LSD usage fell sharply circa 2000. The decline is attributed to the arrest of two chemists, William Leonard Pickard, a Harvard-educated organic chemist, and Clyde Apperson. According to DEA reports, black market LSD availability dropped by 95% after the two were arrested in 2000. These arrests were a result of the largest LSD manufacturing raid in DEA history.

Pickard was an alleged member of the Brotherhood of Eternal Love group that produced and sold LSD in California during the late 1960s and early 1970s. It is believed he had links to other "cooks" associated with this group — an original source of the drug back in the 1960s — and his arrest may have forced other operations to cease production, leading to the large decline in street availability.

The DEA claims these two individuals were responsible for the vast majority of LSD sold illegally in the United States and a significant amount of the LSD sold in Europe, and that they worked closely with organized traffickers. While this claim may have some bearing, the extent of Pickard's direct influence on the overall availability in the United States is not fully known. Some attest that "Pickard's Acid" was sold exclusively in Europe, and was not distributed through American music venues.

In November of 2003, Pickard was sentenced to life imprisonment without parole, and Apperson was sentenced to 30 years imprisonment without parole, after being convicted in Federal Court of running a large scale LSD manufacturing operation out of several clandestine laboratories, including a former missile silo near Wamego, Kansas.

LSD manufacturers and traffickers can be categorized into two groups: A few large scale producers, such as the aforementioned Pickard and Apperson, and an equally limited number of small, clandestine chemists, consisting of independent producers who, operating on a comparatively limited scale, can be found throughout the country. As a group, independent producers are of less concern to the Drug Enforcement Administration than the larger groups, as their product reaches only local markets.

See also

• ALD-52
• Bogle-Chandler case, deaths mistakenly attributed to LSD overdoses
• Drug urban legends
• Entheogen
• List of notable psychedelic self-experimenters
• Project MKULTRA, Central Intelligence Agency mind-control research program that began in the 1950s.
• Psychedelics in popular culture
• Psychedelic psychotherapy
• United States v. Stanley, US Supreme Court case
• Related chemical compounds: ergolines, LSA, psilocybin, DMT, serotonin

References

1. Video of the experiment can be viewed here.
2. ^ Cite error: The named reference tihkal was invoked but never defined (see the help page).
3. Li Z., McNally A. J., Wang H., Salamone S. J. (1998). "Stability study of LSD under various storage conditions". J Anal Toxicol. 22 (6): 520–5. PMID 9788528. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
4. ^ "LSD in the US – Manufacture", DEA Publications.
5. Honig, David. Frequently Asked Questions via Erowid.
6. "Street Terms: Drugs and the Drug Trade". Office of National Drug Control Policy. 2005-04-05. Retrieved 2007-01-31. {{cite web}}: Check date values in: |date= (help)
7. Seper, Jerry. "Man sentenced to life in prison as dealer of LSD". The Washington Times 27 November 2003.

Further reading

• Aldous FAB, Barrass BC, Brewster K, et al. "Structure-Activity Relationships in Psychotomimetic Phenylalkylamines," Journal of Medicinal Chemistry, Vol. 17, 1100–1111 (1974)
• Grof, Stanislave. LSD Psychotherapy. (April 10, 2001)
• Lee, Martin A. and Bruce Shlain. Acid Dreams: The Complete Social History of LSD: The CIA, the Sixties, and Beyond

External links

• Belfast Telegraph Dr. Albert Hofmann - The father of LSD
• Salon.com: Dr. Hofmann's problem child turns 58, April 16, 2001
• "Spontaneous pattern formation in large scale brain activity: what visual migraines and hallucinations tell us about the brain", lecture by Jack Cowan (via the Internet Archive)
• "Hofmann's Potion: The Early Years of LSD" by the National Film Board of Canada
• Erowid -> LSD Information
• A Critical Review of Theories and Research Concerning LSD and Mental Health
• The Neurochemistry of Psychedelic Experience, Science & Consciousness Review
• Current LSD Research – MAPS
• International 3 day conference on LSD in Basel
• The Lycaeum Archive -> LSD
• FRANK - LSD

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