Salvinorin A pharmacology and related physiology

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Salvinorin A pharmacology and related physiology

Postby Ulmdorgr » Tue Jun 01, 2010 11:19 am

Last updated: June 2, 2010.

Salvinorin A
  • Molecular formula: C23H28O8.
  • Molar mass: 432.46 g/mol.
  • Melting point: (242-244)–(238-240)°C (-165-162 °F) - I'm looking for a reference on this one.
  • Boiling point: 760.2 °C (1400 °F) - a typical lighter flame burns around 1100°F (a butane torch can double that; glass melts around 4000°F).
  • Density: unknown.
  • Classification: trans-neoclerodane diterpenoid.
    • Non-alkaloidal, non-nitrogenous (atypical hallucinogen).
  • Hallucinogenic classification: dissociative.
  • Solubility: organic solvents (ethanol and acetone), slightly in water (see Detectable locations below), not soluble in fat (your body will not store it).

Pharmacology
  • Effective Dose: 200–1,000 μg (0.0002-0.001 g).
  • Lethal Dose 50 (LD50): unknown. Higher than THC. Mice given chronic injections for two weeks, with doses that were 5-700 times larger than a human dose, did not die within two weeks (after that they were killed and disected). "Doses were 400, 800, 1600, 3200, or 6400mcg/kg or a volume of vehicle equivalent to that of the 1600mcg/kg group to serve as control" (highest dose was about 2.9mg/lb). "Salvinorin A was prepared for injection by dissolving 1mg of salvinorin A in 10µl of DMSO and then adding 10ml of water to produce a fine suspension suitable for injection." "Valdes et al (5) reported that a single injected dose of 1g/kg did not have any apparent toxic effects in mice, although histology or other objective evaluation was not provided." See reference #2. The study is flawed because the weight of the mice is not noted; only age and gender. Here's one company's mouse weight chart (for the type of lab mice used in this study): http://www.criver.com/SiteCollectionDoc ... 1_mice.pdf
  • Detectable locations: blood plasma, saliva, and urine. Possibly (not determined through research) in sweat if large amounts are consumed.
  • Detection limit: 5 nanograms (0.005µg).
  • Metabolism analysis: 580 micrograms (0.58mg) of smoked Salvinorin A translates to:
    • 11.1-25 µg/L (about 1.9-4.3% of the amount consumed) in Saliva after 1 hour.
    • 2.4-10.9 µg/L in urine (about 0.4–1.2% of the amount consumed) between 0 and 1.5 hours after consumption.
      • Thus, a dose of 24mg (24,000 µg; my highest theoretical consumption) of smoked Salvinorin A should translate to 456-1032 µg/L in Saliva after 1 hour, and take about 2 hours to reach a similar level as the 580µg dose.
  • Summary of physiological effects:
    • inhibition of intestinal motility: combats diarrhea; this is somewhat contradictory to the effects on AVP (see KOR stimulation below).
    • heart rate/blood flow increase: a slight raise occurs, is said to be "neuroprotective against" hypoxia and ischemia.
    • Effects from KOR (see Selectivity below) stimulation:
      • Inhibition of arginine vasopressin (AVP; a.k.a. Anti-Diuretic Hormone or ADH): causes sweating and, less commonly, urination (yes, some people pee their pants). In the kidney, inhibition of AVP increases saline water in the collecting tubules. Where sodium ions go, so does water.
      • Spinal analgesia (loss of motor control).
      • Sedation (relaxation or sleep/black out inducing).
      • Miosis (pupil constriction).
      • Dysphoria (confusion, deja vu, loss of a sense of time).
    • D2R related effects (see Selectivity, below).

Selectivity

References
  1. Wikipedia.
  2. Mowry M, Mosher M, Briner W (2003). "Acute physiologic and chronic histologic changes in rats and mice exposed to the unique hallucinogen salvinorin A" (PDF). J Psychoactive Drugs 35 (3): 379–82. PMID 14621136.
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Re: Pharmacology and related physiology of Salvia

Postby Ulmdorgr » Tue Jun 01, 2010 11:19 am

Last updated: June 2, 2010.
Data to be studied
  • Density of Salvinorin A.
  • Teratology of Salvinorin A (long term/developmental effects).
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Re: Salvinorin A pharmacology and related physiology

Postby ChemistKen » Tue Jun 01, 2010 11:21 pm

One addition...

Salvinorin A, has been reported to be the most potent, naturally occurring hallucinogen known, with effective doses of 200–1000 μg in humans (Valdés, 1994; Siebert, 1994).
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Re: Salvinorin A pharmacology and related physiology

Postby Ulmdorgr » Tue Jun 01, 2010 11:59 pm

"Potency" isn't measurable and that statement has been used to misrepresent the chemical. LSD has a lower effective dose at 20–30 µg. http://www.ncbi.nlm.nih.gov/pubmed/13497365 or http://archneurpsyc.ama-assn.org/cgi/co ... y/79/2/208
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Re: Salvinorin A pharmacology and related physiology

Postby PipeGnome » Wed Jun 02, 2010 9:49 am

Lethal Dose 50 (LD50): unknown. Higher than THC. Mice given injections 800,000-6.5 million times larger than a human dose did not die.
:!: that is an absolutely amazing piece of information!! i couldnt even begin to comprehend how a dose that high would act on my brain.
have you done any reading on ethoxymethyl salvinorin b (symmetry)? i would like to see some more info on that too.
Last edited by PipeGnome on Wed Jun 02, 2010 10:09 am, edited 1 time in total.
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Re: Salvinorin A pharmacology and related physiology

Postby PipeGnome » Wed Jun 02, 2010 10:07 am

wow, i just saw that they have salvinorin all the way down to "j".
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Re: Salvinorin A pharmacology and related physiology

Postby ChemistKen » Wed Jun 02, 2010 10:34 am

is true Ulmdorgr, however i think that statement refers to a natural potency, and yes lsd no doubt has effects at low concentrations <50micrograms, but most take lsd in much higher amounts where it is very destructive to the human brain....

And yes there are other salvinorins which are produced but none of them have the same effect as salvinorin A, remembering that the stereochemistry and substituents of the salvinorin molecule make a huge difference on how it interacts in the body...and yes there has been some experimentation on mice which show that ultra high concentrations without doing much permanant damage...and salvinorin B has no known effect similar to salvinorin A, this is do to the fact that the acetyl group(COCH3) on sal A is replaced with a hydrogen in sal B...

Exhibit A(Salvinorin A)
salvinorin a.jpg
Image produced by myself
salvinorin a.jpg (7.35 KiB) Viewed 3404 times


Exhibit B(Salvinorin B)
salvinorin b.jpg
Image produced by myself
salvinorin b.jpg (6.88 KiB) Viewed 3404 times
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Re: Salvinorin A pharmacology and related physiology

Postby Ulmdorgr » Wed Jun 02, 2010 10:57 am

Ah I see. I edited your original post and bolded the part that important qualifier.

I'm not very good at reading those molecular structure drawings. The only part that I see changed is on the left side, where the double bonded O and the line on the left are replaced by an H. What do those lone lines refer to; extra electrons? Are there atoms in the drawing that aren't listed by a letter?

@Pipe: no I haven't looked into that. Were you thinking of something like this? http://www.erowid.org/chemicals/salvino ... cle1.shtml
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Re: Salvinorin A pharmacology and related physiology

Postby PipeGnome » Wed Jun 02, 2010 11:07 am

i only knew of Salvinorin A, B and 2-EtOMe-Sal B untill today, i had no idea they had been manufacturing all of those other ones. i know that salvinorin b thru j by themselves are non-active, but they have 2 derivatives of salvinorin b: 2-Ethoxymethyl salvinorin B known as symmetry, and 2-Methoxymethyl salvinorin B, being weaker than symmetry, but stronger than Salvinorin A. the effects are different, but still very intense. there isnt a lot of information on these 2, but its there.
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Re: Salvinorin A pharmacology and related physiology

Postby PipeGnome » Wed Jun 02, 2010 11:10 am

yes, ive seen that one, but there doesnt seem to be a whole lot more than whats on erowid. if any, its bits and pieces that look like they were taken right from erowid and scrambled around a bit. maybe im just not lookin in the right place.
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Re: Salvinorin A pharmacology and related physiology

Postby Ulmdorgr » Wed Jun 02, 2010 11:27 am

I thought A-F were naturally occurring.
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Re: Salvinorin A pharmacology and related physiology

Postby PipeGnome » Wed Jun 02, 2010 11:31 am

they probably all are, i just found out about them. interesting stuff. i like this page you are doing. have you read the encyclopedia of psychoactive plants by christian raatsch? you'd probably love it.
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Re: Salvinorin A pharmacology and related physiology

Postby Ulmdorgr » Wed Jun 02, 2010 11:44 am

I don't have any good books yet. I've been buying a lot of new age/religious stuff lately, rather than chemistry, biology, or psychonautics books. Someday!

I've seen that book before, but I didn't have it on my list of stuff to buy, so now I've added it. Thanks.
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Re: Salvinorin A pharmacology and related physiology

Postby Ulmdorgr » Wed Jun 02, 2010 12:06 pm

I need some help analyzing the LD50. I've put some notes in there, and there's a reference to the study at the bottom (the PDF is link and its free). I'm confused as to whether they took a mouse, weighed it, then used their dose (i.e. 6400 micrograms) and divided it by the weight of the mouse, then injected the mouse with that tiny dose. I'm hoping that they took 6400 micrograms, placed it into a liquid mixture, diluted it, then injected all of it over a period of time.

Micrograms/kg seems like a stupid unit. It should be micrograms/L or some other volume because the density of Salvinorin A is unknown.
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Re: Salvinorin A pharmacology and related physiology

Postby ChemistKen » Wed Jun 02, 2010 1:24 pm

salvinorin a1.jpg
salvinorin a1.jpg (8.78 KiB) Viewed 3624 times


The above structure shows the carbons and hydrogens not shown in the line drawing, and yes each line represents a bond(2 shared electrons) and bold or dashed wedges simply illustrate stereochemistry. The acetyl group is thought to be responsible for salvinorin A's affinity for the receptor and therefore its effect.

And as far as the mice thing, what they did is extract and purify salvinorin A from crushed dried leaves using simple laboratory techniques that are used quite often in chemistry. The dissolved the salvinorin A crystals and diluted with water. The stated dose was injected into the mice everyday for 14 days, i.e. 14 doses of 6400mcg over 2 weeks(total of 89.6mg over 14 days) for the highest dose. Whats amazing is that there seemed to be little to no damage due to this...and the studies showed that the only adverse effect is a potential, and very slight, increase in pulse pressure(blood pressure). Yet they did not study the teratogenic effect of salvinorin A...possibly a research area if I were a biologist...and the LD50 is still unknown...possibly extremely high...

Well good thing we have a chemist here like me :P , and also mcg/kg is an acceptable unit and seems to refer to the dosage(i.e. the amount of salvinorin A per the size of the test subject) and not to the concentration as mcg/L would. Also the density of salvinorin A does not need to be known to calculate the mcg/kg or mcg/L...density of salvinorin A would only need to be known to calculate units like ml/kg or ml/L or anytime when weight of salvinorin A would be expressed in volume of salvinorin A. Thanks for the article though...I find there extraction and purification of salvionorin A of interest because it is rather simple...
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