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Doc 0000151832

CIA

This document, part of the CIA MKUltra mind-control program collection, appears to be a scientific paper detailing the chemical structure and properties of psilocybin, noting its relationship to lysergic acid and bufotenine.

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The image displays the title "THE BLACK VAULT" superimposed on a stylized graphic of a bank vault door. Below the title, white text explains that the document was obtained from The Black Vault, an online database of declassified government documents, specifically concerning the MKULTRA/Mind Control Collection, which houses over 20,000 declassified pages from the CIA. The text further provides a URL for downloading the collection. The left side of the image features a portion of the aforementioned bank vault graphic, rendered in cool blue and metallic tones, complete with complex locking mechanisms and a dial. There are no photographs of people, locations, equipment, or subjects. There are no handwritten annotations, signatures, marginalia, official stamps, forms with filled-in fields, diagrams, schematics, organizational charts, tables, structured data, or redations. -. ........ . . .- · .... . ---.. . .. ... . . . . . . .. . . . . ~ . . . . . .. . . . . . . ~ . - . · v ~ . . . - .. . . . . ~ - -· .. - .. - .. - · · ~ - -- - .. • - #....- ; ---~ ""' , ... . .J ~ .... ar..d .:--.;lo::" reo.ctions, h~~n revealed. that it is a.."l indole dariv~.-t.ive, sub~t.it.uted in tal 'bt~;!=;;:no tr.lcl~::.3. It iriaS proYisionally assi~~d ~tho !oz::ula: cl.)~S(20)0.3I!2?2' b~~ l1r. l::.t.•:lr d~zr~d:?.t.icn studies luv-e 3ho~.a it to be c 12 E 1 r[J 4 Cn h}"'d..rol]'sis the psil~=-foin ~ol·3~ula is cleavod i."l t~-o, ~-riving; 4-hydrO.:q-±il:eth7ltr'1P't~a and phozph- orl~ acid.. Th<r.:.s psllocrbin ~s~esses th3 structural !omula I. I. OH 6o H 0 z > . N A It is t~~ pho~phor.ic estor ot 4-h~~ethyltrypt~"le. Thia constitution h~ be~~ ,.· -· - ( - . - 3 ~ -/ - _ · ., ) .. . .--· --- -··- , - l ,... ... . ' ':'\ ~- · b'.!!'vt•~::t.i..""l {5:-h;:·;:"i.rc~.~t!::j·lt!7i-!.a~-;,n~), bu!ot.enidine(qUarternar:r base ot btl.fotellin) . <Uh7d:oo-b~ot,·r-..i.."l !?-."'ld bu!oth!o~ino. 'ni=l struetura Cll'l~ogy 'With bufothioni."li3(!or:ul.J. I!) . 7) • ,.,,;~""h ha!3 b~c:l.i::~l~ted !ror:l a=l"'hibian ~~in is strfkin·~. I--· r - n. EP eo~ so- ~r-CH:CH­ .,r oJ ~~' I H ester o£ acid, other of acid. t~~g ~, ~1osphoric ~~e ~·ilfuric ~·s~seial relationship ~~sts bet~e~ p~iloc~in and lj~ergic aeid c.::;.da an i.."ldolo C.13l"ivati7<9G subst.itu.tad in pos!tion 4. Psilocybin ~d the ergot ............. .. ~ ~ • p.:ll~t,;7b:i:1 ~;)!c~ul.e ~pl.ie3 c.=tiv::Ltion ot po:3ition 4, it C.oes not see:n U.:."lroacona~.lJ ! _ -- _ -'" _ . " ,. '-· . .. ; . · · ~ ~ . ~ o. , - . - .. ... . .. ~-. t _ . , J . . . ~ ....,. -~· -' ----~----------------· ~-··~-~ ~- .. ---... --.... ... ----- J. -~ - ..... --·-·- 1) VJ..L:~n'!:!A ?. \lASSCN and R.G. ~':'. . l.SSO:i~ ~.tshrcc~s, Russia :.nd H.1sto27 (?n.ntteon .Books, Ue1.., Yo~~ 1957). C.R. Aead.Sci ~' 1JS9 (1956);~1695 {l?57)J 2) It. HB"l1·1, P.ovue cs Myeo1ogie ~~ Z0,36 (19;?). 3) R. HEIU a::1d R. C/.ITJ %'1, C.R. J.c.:.d.Sci ~,3109 (19;'7); ~i,577,176l (1957). 4) A. E0::'!!:\.1:!l, P.. HE!;l, A. BR.\C~ u.ad H. KC2ZL, Expericntia. (1958). ~,l07 c.a. Acad:se~ 2L6, 1346 (1953). TRon.:::a, Ue1.., Yo~~ 1957). C.R. Aead.Sci ~' 1JS9 (1956);~1695 {l?57)J 2) It. HB"l1·1, P.ovue cs Myeo1ogie ~~ Z0,36 (19;?). 3) R. HEIU a::1d R. C/.ITJ %'1, C.R. J.c.:.d.Sci ~,3109 (19;'7); ~i,577,176l (1957). 4) A. E0::'!!:\.1:!l, P.. HE!;l, A. BR.\C~ u.ad H. KC2ZL, Expericntia. (1958). ~,l07 c.a. Acad:se~ 2L6, 1346 (1953). TRon.:::a, 6) E%perientia ~~·~· (1956) in press. voc:m, 7) ii. 'ii!0!..:\!ZD, !i'. A. ~.Q1,216 (1930). ·. !·r~1!cul. D~~~~~nt :: ._·:.:: l.J z F:: :--.:.~-"lceu ti c~s tJ- -.:t. / __ - - , .. ·-.. ... ___ ·- ..____ - ~· ·~ ., I ~ - ; _ _ ______ ..-.,_.;.., • !I ®f --<=Er. -~-,-cr-'-3 CI!3 E:..~i...-icnl i"o:r::::.us.: c12=17~rr2P • . ~c:I . 0.:1. Iro3• of P.ailocybiu d.1s5ol-nt ill 1 c:c:. 0.01~ :t"en'"ic • Tiol-ot.eolor ia obtained• .... - ••· • • • -. -t 4 . j - ... lJ ---: ;·I .'. . --·--------- ---·-- ·• The image is a declassified document containing text and some visual elements. There is a handwritten number "141" in the upper right corner, possibly a page number. Additionally, there's a handwritten annotation "B-74" in the lower right corner. The document appears to be a research paper or scientific article, with titles and author information clearly visible. There are no photographs of people, locations, equipment, or subjects, nor any diagrams, schematics, or organizational charts. There are no official stamps nor any evidence of experimental procedures, equipment, or facilities visually depicted on this page. The majority of the page is filled with typed text, with some faint lines that may have been part of an original layout. The document contains a handwritten scientific report detailing the chemistry of psilocybin. It includes chemical structures, reaction schemes, and formulas that illustrate the synthesis and degradation of the compound. There are no photographs, official stamps, or forms with filled-in fields. The document features handwritten marginalia at the top and a page number "B-73" at the bottom right. There is some redacted content at the top of the page. The document is a scanned page from a typewritten report with a chemical diagram. At the top, there's a faint indication of a circular stamp and some horizontal lines. The main body contains dense text. Prominently displayed is a chemical structure labeled "II," showing indole and other related functional groups. There are also some handwritten annotations, including a number "7)" near the diagram and a circled "II" to the left. Along the bottom right, there is a handwritten notation "B-72". The document appears to be a typed page from a bibliography or list of references, titled "Literature." It contains a numbered list of seven entries, each citing authors, titles, and publication details. There are no photographs, diagrams, forms, or tables. The only visual elements beyond the typed text are a few scattered dark specks, likely printing imperfections, and a handwritten annotation "B-71" in the bottom right corner. There are no official stamps or visible redactions. The page displays chemical information related to a compound called "o-phosphoryl-4-hydroxy-N,N-dimethyl-tryptamine," including its molecular structure diagram, empirical formula, molecular weight, melting point, solubility, and pH. It also records the "Keller Color Reaction" procedure and its results, describing the addition of a ferric chloride solution and concentrated sulfuric acid, which yields a "permanent violet color." There are handwritten annotations at the bottom likely indicating a document number or code ("B-70") and possibly an organizational affiliation ("Candor Pharmaceuticals, Medical Department"). No photographs, stamps, or evidence of experimental procedures are present.

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