ephedra nevadensis - what is the pseudoephedrine content

loki · guinea pig

there's been a lot of flurry surrounding ephedra sinensis because it contains ephedrine, but for the person interested in synthetic modifications of ephedrine type alkaloids, it is irrelevant whether the hydroxyl swings to the left or right.

one thing that has come to my attention while addressing questions about separating ephedrine from an ephedrine/ethylmorphine combination medicine was that ephedrine freebase is fairly soluble in water. I have attempted to isolate ephedrine on two occasions once from sinensis extract and once from raw sida cordifolia herb, to no avail, and i have been wondering why. now i think i know what the reason is - ephedrine's solubility as freebase is not what i thought it was.

i have been searching for information about ephedra nevadensis alkaloid content, and i came across only a few references to it even having pseudoephedrine in it, and of the references, i found nothing stating alkaloid content. Which i find most disappointing. Because, as I said before, when it comes to synthetic derivatives in which the beta hydroxyl is modified via reduction or oxidation, it matters not which chirality the hydroxyl is in, both end up with non-chiral modifications (one removing the hydrogen, the other removing the oxigen).

it seems to me that pseudoephedrine is the much more viable alkaloid to attempt to extract from plant sources, some kind of modification of the new straight to bee III type extraction involving extracting the freebase into hot naptha and precipitating it out in the freezer.

before swim goes and blows his money on a pile of ephedra nevadensis 1:4 extract, he would like to know if anyone can point swim to or give the answer to the question of how much alkaloids it has in it.

loki · guinea pig

i thought i might add some new (old) information to this post from stuff i gleaned from reading the document 'the preparation and properties of ephedrine and its salts' with regard to methods to effectively isolate ephedrine or pseudoephedrine from plant material.

i will summarise whan i worked out from reading it:

ephedrine can be isolated from the crude alkaloid extract via the formation of the oxalate salt. ephedrine oxalate is only sparingly soluble in water and precipitates out in cold water.

pseudoephedrine can be isolated from the crude alkaloid extract by forming the oxalate and precipitating it from alcohol.

here are the important solubility characteristics relevant to isolating the alkaloids:

loki · guinea pig

EPHEDRA/ MORMON TEA (Ephedra nevadensis)

INTRODUCTION :
Ephedra, an evergreen perennial herb that grows in the South-Western deserts of America and in some parts of china, is valued for its healing and stimulating properties for at least 5000 years. In ancient china it was used for its medicinal qualities. Asthma, fever and colds were treated with Ephedra or 'ma huang'. Mormon sects, who are not allowed to drink coffee because of religious conviction, use Ephedra nevadensis as a coffee substitute. 'Mormon tea' stimulates differently and has more sexual stimulating effects than coffee, Ephedra is therefore used in tantric rites as a sexual stimulant. Since isolation of ephedrine from several Ephedra species, in the early 1920s, ephedrine became a popular drug for the treatment of asthma. It also counteracts the symptoms of narcolepsy, and has ability to calm hyperactive children.

EFFECTS :
Alerting, stimulating, greater mental and physical endurance, euphoria, appetite supression, insomnia. These 'adrenaline like' effects enable an animal to respond more rapidly to predatory threats : ephedrine speeds the heartrate, increases blood pressure, muscular strength and dilates the bronchial tree. Occasional, moderate use of Mormon tea has no toxic effects on humans, unless see 'Dangerous combinations' When Mormon tea (ephedrine) is used in very high doses or chronically, anxiety, nervousness and psychotic reactions can occur. The psychotic reactions resemble paranoid schizofrenia.

DURATION :
4-7 hours. USAGE : 5-15 grams of Ephedra is needed for the preparation of 1 litre of Mormon tea. Add the Ephedra to 1 litre of water, then let it boil for approximately 10-15 minutes. The desired effect will be reached with 200-400ml (on the basis of 12 grams of Ephedra nevadensis).

Dosage and preparation
5-15 grams of E. nevadensis is needed for the preparation of 1 litre of Mormon tea, but merely 1-3 grams when the plant material is ingested.
E. Sinica may also be prepared as a tea (1.5- 9 grams) and otherwise it is physiologically active in doses of 0.5-1.5 grams. 5
A stimulating tea can be prepared by adding the plant material to 1 litre of water and letting it boil for approximately 10-15 minutes. The desired effect will be reached with 200-400ml (on the basis of 12 grams of Ephedra nevadensis). A stimulating dose consists of 10-15 milligram of ephedrine.

Figure: Dried Ephedra stems

Botanical aspects
E. nevadensis, a member of Ephedraceae, finds its origin in South-West America. E. sinica is native to northern China.
This plants don't have leaves, but are consist of green cylindrical segments that form 90 cm long 'tubes' that branche extensively. Ephedra species can be reproduced vegetatively (by root division), but propagation through seeds is far more usual. For this purpose the seeds require a warm klimate (20-25 °C) and a mumid environment. The germination periode usualy lasts 1-3 weeks.

Phytochemistry
L-ephedrine (phenylpropanolmethylamine), d-pseudoephedrine and norpseudo-ephedrine and norephedrine are present in several Ephedra species. 5, 7 Dried E. sinica contains 1.0-2.5 % alkaloids and other minor constituents of E. Sinica are saponines and flavonoids (vicenine, lucenine).

Table 1.12: phenylisopropylamine derivatives (PIPA's)
Trivial names Formal names
(-)-Ephedrine 1R,2S N-methyl, b-hydroxy-PIPA
(+)-Pseudo-ephedrine 1S,2S N-methyl,b-hydroxy-PIPA
(-)-Norephedrine 1R,2S,b-hydroxy-PIPA
(+)-Norpseudoephedrine 1S,2S,b-hydroxy-PIPA

Pharmacology
All active principles are structurally related to norepinephrine (noradrenaline) and dopamine. Due to the similar chemical structures, ephedrine molecules act as indirect sympathomimetica; ephedrine's stimulating effects are modulated by five different places of action. 1 One, ephedrine is substrate for Na+-dependent noradrenergic-transporters in the synaptic membranes and thereby it competitively inhibits the noradrenaline uptake from extracellular space into the axoplasma. As a result, more adrenergic ß-receptors are activated. Second, ephedrine inhibits the uptake of noradrenaline from the axoplasma into the synaptic vesicles due to an affinity for the noradrenergic-transporter protein in the synaptic vesicle membrane. Three, normally noradrenaline would be quickly inactivated by MAO (monoamine oxidase), but due to the presence of ephedrine (which is also substrate for MAO) its inactivation is postponed and also leads to an increased concentration of noradrenaline in the axoplasma. Four, noradrenaline in the axoplasma cannot cross the synaptic membrane itself (due to its lipophobe character), but is transported through the membrane by Na+-dependent noradrenaline-carrierproteins; the noradrenaline from the axoplasma reaches the extracellular space through a non-exocytotic co-transport with Na+.
Five, noradrenaline is usually inactivated by a reuptake process back into the nerve endings, but because ephedrine is also substrate for these transporter-proteins, again noradrenaline is competitively inhibited, which in turn leads to a further increased noradrenaline concentration in the extracellular space, thus stimulating the exitatory receptors of the post-synaptic cell for relatively longer time.

MODIFIERS :
- Ascorbic acid (vitamine c) reduces ephedrine's effects.
- Ephedra should not be combined with MAO-inhibitors1.
- Ephedrine is positive synergistic with caffeine, magic mushrooms and general psychedelics1, 3.
- Ephedrine counteracts the effects of alcohol5.

DANGEROUS COMBINATIONS :
NEVER use Mormon tea in combination with MAO- inhibitors, high bloodpressure, or when one suffers from psychotic depressions. Stimulants, like ephedrine, intensifies the bloodpressure increasing effect of MAO-inhibitors (Peganum harmala: harmine, harmaline, high doses of pasion flower, prozac), and in general make depressions worse.

References
1. [Forth/ Henschler/ Rummel/ Fostermann/ Starke, 2001]
2. [Gotlieb]
3. [Hoffer/ Osmond, 1967]
4. [Hoffmann/ Schultes, 1973]
5. [Ratsch, 1998]
6. [Rattray, 1991]
7. [Snyder, 1996]

(Text by Wout. Please mail here for your comments)

dwarfer · Tue Jul 12, 2005 3:16 am

Little or no ephedrine alkaloids in Nevadensis or similar. Some New Mexico variety shorter bushes on S. sloping hills near washes N of Lordsburg, however, are reputed to beat this generalized observation.

Extraction of other alkaloids, however, and subsequent reduction, will generate effects worthy of mention.

It has been proven that the phenylalanine molecule is the precursor structure used by Ephedra to make ephedrine.

consideration should be given to performing an experiment with which a few healthy specimens are provided with a solution including dissolved Phenylalanine:
or maybe just dump some NutraSweet around their roots.

check for increased ephedrine alkaloids yearly..

wouldn't that be clandestine: to have a few 8 foot tall plants that you secretly had adopted, and were having a love affair with...??

loki · guinea pig

hehe lol dwarfer...

yeh precursor feeding is a proven technique in numerous organisms.

so are you saying that nevadensis contains or does not contain pseudoephedrine? (do you mean pseudo/ephedrine when you say 'little or no ephedrine alkaloids'?)

I definitely would have a love affair with a plant which produces beta hydroxy alpha methyl phenethylamines Wink

dang just gotta organise which one i want, hence the topic, i am not concerned with the chirality of the hydroxyl one bit, in fact the pretending chirality would be better due to it's lack of association with the plant, most people don't think about it that way: plant=ephedrine pill=pseudo. thus plant + pseudo = wtf