Date: Thu, 18 Dec 1997 19:26:07 EST
From: Chris Jenks <>
To: Multiple recipients of list <>
Subject: TIHKAL Section About Ibogaine

  Dear Everyone,

  I have now reached the description of ibogaine in my reading of TIHKAL.
Here is the text, from pp. 487-490:


SYNTHESIS: There have been three total syntheses of ibogaine reported in
the chemical literature. The first of these was a thirteen-step process
published about 30 years ago. The chemistry lab can serve a fine function
for both isolation and purification of ibogaine from plant sources, but in
the real world, there is no practical way to start from a bottle of
nicotinic acid and actually prepare useful amounts. The parent ring system
contains two chiral centers, neither of which is amenable to easy
manipulation. Because of these two separate and largely inaccessible chiral
centers there are, in theory, four distinct isomers of ibogaine which are
difficult to resolve. When the term "synthetic" is used in regard to
ibogaine in the scientific journals, it usually applies to the resynthesis
of the parent alkaloid from the demethylated metabolite. For reference
purposes, here are the fingerprint numbers from the infrared spectra: for
the free base: IR (in percentimeters): 741, 799, 830, 1037, 1111, 1148; mp
152-153 degrees Celsius. For the hydrochloride salt: IR (in
percentimeters): 638, 810, 832, 925, 1031, 1149; mp 299-300 degrees Celsius

DOSAGE: (from hundreds of milligrams up to a gram or more, orally)

DURATION: (quite long)

EXTENSIONS AND COMMENTARY: Here is an example of a most remarkable material
that has allowed people to have some rather complex and dramatic
experiences. Any effort to present a fair overview of its action, through a
selection of individual responses in the "extension and commentary" format
would fail, as it would ignore the impact of the set and setting on the
subject. Here I will mention a few of these different sets, and a leading
author who gives more detail.
  There is a well studied history of the use of the iboga plant in the
religious rituals in Gabon and its neighboring countries, from the early
part of the 19th century. The Buiti religion calls for the use of the root
bark of Tabernanthe iboga as a sacrament, and the reports of its
psychopharmacological effectiveness reflect these needs (see Samorini).
  Another area of reports that can be called upon reflects the exploration
of the isolate from this plant, or the isolated active component ibogaine
itself, in the study of its use with psychotherapy. Here the reports
reflect the physician/patient interaction with an emphasis on early memory
and the reliving of past experiences (see Naranjo). In clinical studies
such as these, a typical dose would be four hundred milligrams of the
chemical, twice this weight of the crude isolate, and perhaps ten times
this weight again if the actual root bark is used.
  Yet another source of reports is to be found in some studies that are
exploring ibogaine as a treatment for heroin dependency (see De Rienzo and
Beal). This end-goal of retrieving evidence of addiction confrontation and
addiction control can certainly color any published reports in its own way.
Here, it is only the chemical ibogaine that is used, and typical dosages
are at or above 1000 milligrams.
  There is no question but that ibogaine is a rough trip, physically as
well as mentally. Here is one report that shows the body aspects of its use.
  (with 200 mg, orally) "Subjectively, the most unpleasant symptoms were
the anxiety, the extreme apprehension, and the unfamiliar mood associated
with visual and bodily hallucinations. The visual hallucinations appeared
only in the dark and consisted of blue disks dancing up and down the walls.
Dysesthesia of the extremities, a feeling of light-weightedness, and
hyperacusis were other symptoms noted. Autonomic signs, such as dryness of
the mouth, increased perspiration, slight pupillary dilation, and increase
in pulse rate, as well as extrapyramidal syndromes (fine tremors, slight
ataxia, enhanced tendon reflexes and clonus) were also present. The peak
effect was reached at about 2 hours after swallowing the drug; it subsided
gradually, leaving as a residue complete insomnia. No undesirable
after-effects, such as exhaustion or depression occurred."
  As was pointed out in a pharmacological review (see Popik et al.), as the
hallucinogenic dose appears to be several times higher than the stimulant
dose, the user must endure intense and unpleasant central stimulation in
order to experience the hallucinogenic effects.
  But as fascinating as the pharmacology of ibogaine, it is the chemistry
of this alkaloid that is overwhelmingly awesome. The presence of four
isomers was mentioned in the chemistry section above, but this fact was not
appreciated until the 1960's and even then, a couple of troublesome errors
were made that confused the absolute configuration picture quite badly. The
story has been accurately told in a (nearly) hundred page review chapter
(see Cordell) which is a must for anyone who wants to risk understanding
some pretty far-out chemistry. Oh my, there are a lot of closely related
alkaloids. As to indolic alkaloids in general, there are well over two
thousand of them, with a few dozen added every year. And most of these are
kosher tryptamines in that they carry the tryptamine structural skeleton.
And, in turn, a great number of the tryptamine alkaloids are found in the
remarkable family Apocynaceae, which is the ultimate treasure-trove of
alkaloids, probably the richest single source of pharmacologically active
compounds in the entire plant kingdom. It is made up, largely, of tropical
shrubs of the dogbane group, which almost always ooze out a sticky sap when
you break off a twig. They have showy flowers, and the reputation of being
very poisonous.
  And this all leads smoothly to the botany, which is almost as convoluted
as the chemistry. Here, let me list the plants that contain ibogaine, or
that should contain it. Allow me a brief run-down of binomials. There is a
number of species that are, or have been, classified as belonging to the
Tabernanthe genus and which are reasonable sources of ibogaine, and which
are logical alternatives, psychopharmacologically, to the iboga plant itself.

  Tabernanthe iboga. This is the major source of ibogaine and is found in
Gabon, mentioned above.
  Tabernanthe orientalis. This plant is now called Ervatamia orientalis,
and is found in Western Australia. The leaves contain ibogaine, along with
six minor alkaloids that are closely related, structurally.
  Tabernanthe pubescens. This is found in Zaire, and contains a number of
alkaloids closely related to ibogaine in structure, as well as ibogaine
  Tabernaemontana spp. This genus if from a tribe within the family
Apocynaceae that is called the Tabernaemontaneae. As an official sub-family
it would be called Tabernaemontanoideae. It is because of the casual use of
names such as these that botanical binomialists are rarely invited to
social functions. It (this Genus, that is) contains several dozen species,
some with ibogaine, many with analgesic or sedative action in experimental
animals, and some with quite a history of native usage either in Africa or
Southeast Asia.

  And there are many plants in the Apocynaceae family that carry
fascinating alkaloids that are closely related in structure to ibogaine and
which, potentially, might have a similar psychopharmacology. In most of
these, ibogaine is present in very small amounts, if at all.

  Anacampta spp. have usually been published as Tabernaemontana spp., as
have been species originally published as part of the Genera Bonafousia,
Capuronetta (which has become the species capuronni under this Genus),
Conopharyngia, Ervatamia, Gabunia, Hazunta, Muntafara, Pagiantha, Pandaca,
Peschiera, Phrissocarpus, and Stenosolen. All of these contain alkaloids
related to Ibogaine.
  Callichilia barteri has appeared as Hedranthera barteri, but C.
subsessilis demands the name Tabernaemontaneae subsessilis in the
presentation of its alkaloid content.
  Creoceras, Rejoua, Schzozygia, Stemmadenia and Voacanga have, with all
their species, remained intact with their original names.
  Peschiera echinata, this is one of some ten species within the
Tabernaemontaneae classification, with some 2% alkaloid content in its
leaves. Ibogaine is present.
  Voacanga schweinfurthii var. puberula (known in the older literature as
Voacanga puberula) contains some ten related alkaloids. The major one,
found in the seeds, and is tabersonine, is present at a rather remarkable
3.5%. Ibogaine is present in the root bark but, at a concentration of 200
mg/Kg (0.02%), it is truly a minor constituent.

Samorini, G., The Buiti Religion and the Psychoactive Plant Tabernanthe
Iboga (Equatorial Africa). Integration #5 105-114 (1995).

Naranjo, C., Ibogaine, Fantasy, and Reality, The Healing Journey: New
Approaches to Consciousness. Pantheon Books, New York. 1973. pp. 174-228.

De Rienzo, P. and Beal, D., The Ibogaine Story; Report on the Staten Island
Project. Autonomedia, New York. (1997).

Popik, P., Layer, R. T. and Skolnick, P., 100 Years of Ibogaine:
Neurochemical and Pharmacological Actions of a Putative Anti-addictive
Drug. Pharmacological Reviews 47 235-253 (1995).